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OXIME ESTER PHOTOINITIATORS

20230142648 · 2023-05-11

    Inventors

    Cpc classification

    International classification

    Abstract

    Disclosed are α-oxo oxime ester compounds based on carbazole derivatives which have specific substituent groups useful as a photoinitiator, as well as photopolymerizable compositions comprising said photoinitiator and ethylenically unsaturated compounds. The photopolymerizable compositions are useful, for example, in photoresist formulations for display applications, e.g. liquid crystal display (LCD), organic light emitting diode (OLED) and touch panel.

    Claims

    1.-21. (canceled)

    22. A compound of formula I, II, III or IV, ##STR00219## wherein R.sup.1 is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.20cycloalkyl, C.sub.2-C.sub.12alkenyl, wherein C.sub.3-C.sub.20cycloalkyl or C.sub.2-C.sub.12alkenyl is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10 or COOR.sup.4; or R.sup.1 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, COOR.sup.4CONR.sup.10R.sup.11, CN, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a, ##STR00220##  C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; or R.sup.1 is C.sub.2-C.sub.20alkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO, SO.sub.2, phenylene, naphthylene or NR.sup.10, wherein the interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more halogen, C.sub.3-C.sub.8cycloalkyl, OH, SH, OR.sup.4, SR.sup.9, COOR.sup.4, O(CO)—R.sup.3a, CONR.sup.10R.sup.11, NR.sup.10R.sup.11, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.1 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl each of which is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, phenyl, halogen, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, COOR.sup.4, (CO)—R.sup.3a, (CO)NR.sup.10R.sup.11, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a or group ##STR00221##  or by one or more C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S, or NR.sup.10; or by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.4, CONR.sup.10R.sup.11, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aryloxycarbonyl, C.sub.3-C.sub.20heteroaryloxycarbonyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; R.sup.1 is C.sub.2-C.sub.20alkanoyl or benzoyl which is unsubstituted or substituted by one or more C.sub.1-C.sub.6alkyl, phenyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.1 is C.sub.2-C.sub.12alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups; or R.sup.1 is phenoxycarbonyl which is unsubstituted or substituted by C.sub.1-C.sub.6alkyl, halogen, phenyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.1 is CN, (CO)—R.sup.3a, COOR.sup.4, CONR.sup.10R.sup.11, NO.sub.2, PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; R.sup.1′ is C.sub.1-C.sub.20alkylene, C.sub.1-C.sub.20alkylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or NR.sup.8, wherein the C.sub.1-C.sub.20alkylene and interrupted C.sub.1-C.sub.20alkylene is unsubstituted or substituted by halogen or OR.sup.4, or R.sup.1′ is C.sub.2-C.sub.20alkenylene, C.sub.2-C.sub.20alkenylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or by NR.sup.10, wherein the C.sub.2-C.sub.20alkenylene and interrupted C.sub.2-C.sub.20alkenylene is unsubstituted or substituted by halogen or OR.sup.4, or R.sup.1′ is C.sub.5-C.sub.8cycloalkylene, C.sub.5-C.sub.8cycloalkenylene, ##STR00222##  wherein the groups C.sub.yH.sub.2y and C.sub.zH.sub.2z are uninterrupted or interrupted by one or more O, S or by NR.sup.10; R.sup.1a is hydrogen, C.sub.1-C.sub.20alkyl, CN, (CO)—R.sup.3a, COOR.sup.4a, CONR.sup.10aR.sup.11a, NO.sub.2, PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; or R.sup.1a is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, CN, COOR.sup.4a, CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a NR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; or R.sup.1a is C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.1a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10a or COOR.sup.4a; or R.sup.1a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—R.sup.3a CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; or by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.4a, CONR.sup.10aR.sup.11a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or by one or more C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.10a; or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; R.sup.2 is hydrogen, C.sub.1-C.sub.20alkyl or C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6-cycloalkyl which is unsubstituted or substituted by one or more halogen, OR.sup.4, SR.sup.9, COOR.sup.4CONR.sup.10R.sup.11, NR.sup.10R.sup.11, PO(OR.sup.3a).sub.2; COR.sup.3a, or R.sup.2 is C.sub.2-C.sub.20alkyl or C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6-cycloalkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO, SO.sub.2, phenylene, naphthylene or NR.sup.10, wherein the interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more halogen, OR.sup.4, SR.sup.9, COOR.sup.4, CONR.sup.10R.sup.11, NR.sup.10R.sup.11; or R.sup.2 is C.sub.2-C.sub.4hydroxyalkyl, C.sub.2-C.sub.10alkoxyalkyl, C.sub.3-C.sub.5alkenyl, C.sub.3-C.sub.8cycloalkyl, phenyl-C.sub.1-C.sub.3alkyl, C.sub.2-C.sub.8alkanoyl, C.sub.3-C.sub.12alkenoyl, benzoyl; or R.sup.2 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl each of which is unsubstituted or substituted by one or more C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, halogen, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, (CO)—R.sup.3a, or by C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S, or NR.sup.10, or each of which is substituted by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.4, CONR.sup.10R.sup.11, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aryloxycarbonyl, C.sub.3-C.sub.20heteroaryloxycarbonyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.2 is a group ##STR00223## R.sup.2′ is C.sub.1-C.sub.20alkylene, C.sub.1-C.sub.20alkylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or NR.sup.8, wherein the C.sub.1-C.sub.20alkylene and interrupted C.sub.1-C.sub.20alkylene is unsubstituted or substituted by halogen or OR.sup.4, or R.sup.2′ is C.sub.2-C.sub.20alkenylene, C.sub.2-C.sub.20alkenylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or by NR.sup.10, wherein the C.sub.2-C.sub.20alkenylene and interrupted C.sub.2-C.sub.20alkenylene is unsubstituted or substituted by halogen or OR.sup.4, or R.sup.2′ is C.sub.5-C.sub.8cycloalkylene, C.sub.5-C.sub.8cycloalkenylene, ##STR00224##  wherein the groups C.sub.yH.sub.2y and C.sub.zH.sub.2z are uninterrupted or interrupted by one or more O, S or by NR.sup.10; R.sup.3 is hydrogen or C.sub.1-C.sub.20alkyl; or R.sup.3 is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.3 is C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10, CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—R.sup.3a, COOR.sup.4, CONR.sup.10R.sup.11 C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.3 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10 or COOR.sup.4; or R.sup.3 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, COOR.sup.4, (CO)—R.sup.3a or SO.sub.2—R.sup.3a; or R.sup.3 is C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more C.sub.1-C.sub.10alkyl, C.sub.1-C.sub.4haloalkyl, halogen, phenyl, C.sub.1-C.sub.20alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.3 is C.sub.1-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sup.10, CO, SO or SO.sub.2; or R.sup.3 is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, COOR.sup.4, (CO)—R.sup.3a or SO.sub.2—R.sup.3a; R.sup.3a is hydrogen or C.sub.1-C.sub.20alkyl; or R.sup.3a is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, CN, COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.3a is C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—(C.sub.1-C.sub.8alkyl), COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.3a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10a or COOR.sup.4a; or R.sup.3a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—(C.sub.1-C.sub.8alkyl) or SO.sub.2—(C.sub.1-C.sub.4haloalkyl); or R.sup.3a is C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more C.sub.1-C.sub.10alkyl, C.sub.1-C.sub.4haloalkyl, halogen, phenyl, C.sub.1-C.sub.20alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.3a is C.sub.1-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2; or R.sup.3a is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—(C.sub.1-C.sub.8alkyl) or SO.sub.2—(C.sub.1-C.sub.4haloalkyl); or R.sup.3a is a group ##STR00225## R.sup.3b is hydrogen or C.sub.1-C.sub.20alkyl; or R.sup.3b is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, CN, COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.3b is C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—(C.sub.1-C.sub.8alkyl), COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.3b is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10a or COOR.sup.4a; or R.sup.3b is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—(C.sub.1-C.sub.8alkyl) or SO.sub.2—(C.sub.1-C.sub.4haloalkyl); or R.sup.3b is C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more C.sub.1-C.sub.10alkyl, C.sub.1-C.sub.4haloalkyl, halogen, phenyl, C.sub.1-C.sub.20alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.3b is C.sub.1-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2; or R.sup.3b is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—(C.sub.1-C.sub.8alkyl) or SO.sub.2—(C.sub.1-C.sub.4haloalkyl); R.sup.4 is hydrogen, (CO)—R.sup.3a, COOR.sup.4a, CONR.sup.10R.sup.11, S(O).sub.m—R.sup.3a or PO(OR.sup.3a).sub.2; or R.sup.4 is C.sub.1-C.sub.20alkyl, which is substituted by one or more halogen, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a CN, COOR.sup.4a, CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a NR.sup.10aR.sup.11a PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; or R.sup.4 is C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10a, CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—R.sup.3a, COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.4 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10a or COOR.sup.4a; or R.sup.4 is C.sub.6-C.sub.20aryl, which is substituted by one or more halogen, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—R.sup.3a, CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a or group ##STR00226##  or by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.4a, CONR.sup.10aR.sub.11a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or by one or more C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.10a; or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.4 is C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—R.sup.3a, CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a or group ##STR00227##  or by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.4a, CONR.sup.10aR.sup.11a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or by one or more C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.10a; or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.4 together with one of the carbon atom of R.sup.1 forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a (CO)—R.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00228##  or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; R.sup.4′ is —(CO)—, —(CO)O—, —(CO)N—, —S(O).sub.m—, —PO(O).sub.2—, or —OP(O).sub.2; R.sup.4a is hydrogen, C.sub.1-C.sub.20alkyl, (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.4a is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)—(C.sub.1-C.sub.8alkyl), O(CO)—(C.sub.2-C.sub.4)alkenyl, O(CO)-phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2—(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl or C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sup.4a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.4a is C.sub.2-C.sub.12alkenyl, (CO)O(C.sub.1-C.sub.8alkenyl) or C.sub.3-C.sub.8cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); or R.sup.4a is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)—C.sub.1-C.sub.8alkyl or (CO)N(C.sub.1-C.sub.8).sub.2, phenyl or benzoyl; or R.sup.4a is C.sub.1-C.sub.20alkanoyl, C.sub.3-C.sub.12alkenoyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, C.sub.6-C.sub.20aryl, C.sub.1-C.sub.20alkoxy, C.sub.6-C.sub.20arylC.sub.1-C.sub.20alkyl, hydroxyC.sub.1-C.sub.20alkyl, hydroxyC.sub.1-C.sub.20alkoxyC.sub.1-C.sub.20alkyl, C.sub.3-C.sub.10cycloalkyl, amino, CN, NO.sub.2, hydroxy, ##STR00229##  (CO)—R.sup.3a, OR.sup.4a or COOR.sup.4; R.sup.9 is hydrogen or C.sub.1-C.sub.20alkyl; or R.sup.9 is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, CN, COOR.sup.4a CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a NR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; or R.sup.9 is C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—R.sup.3a, COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.9 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10a or COOR.sup.4a; or R.sup.9 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—R.sup.3a CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a or group ##STR00230##  or by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.4a, CONR.sup.10aR.sup.11a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or by one or more C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.10a; or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.9 together with one of the carbon atom of R.sup.1 forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a (CO)—R.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00231##  or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; R.sup.9a is hydrogen or C.sub.1-C.sub.20alkyl; or R.sup.9a is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)—(C.sub.1-C.sub.8alkyl), O(CO)—(C.sub.2-C.sub.4)alkenyl, O(CO)-phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2—(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl or C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sup.9a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.9a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); or R.sup.9a is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)—C.sub.1-C.sub.8alkyl or (CO)N(C.sub.1-C.sub.8).sub.2, phenyl or benzoyl; or R.sup.9a is C.sub.1-C.sub.20alkanoyl, C.sub.3-C.sub.12alkenoyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; R.sup.10 and R.sup.11 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, S(O).sub.m—R.sup.3a, O(CO)—R.sup.3a(CO)—R.sup.3a or CONR.sup.10aR.sup.11a; or R.sup.10 and R.sup.11 independently of each other are C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, CN, COOR.sup.4a, CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a PO(OR.sup.3a).sub.2 or S(O).sub.m—R.sup.3a; or R.sup.10 and R.sup.11 independently of each other are C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—R.sup.3a, COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.10 and R.sup.11 independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10a or COOR.sup.4a; or R.sup.10 and R.sup.11 independently of each other are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—R.sup.3a CONR.sup.10aR.sup.11a, PO(OR.sup.3a).sub.2, S(O).sub.m—R.sup.3a or group ##STR00232##  or by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.4a, CONR.sup.10aR.sup.11a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or by one or more C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.10a; or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.10 and R.sup.11 independently of each other are C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.10 and R.sup.11 independently of each other are C.sub.1-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2; or R.sup.10 and R.sup.11 independently of each other are C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a COOR.sup.4a, (CO)—R.sup.3a or SO.sub.2—R.sup.3a; or R.sup.10 together with one of the carbon atom of R.sup.1 forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a (CO)—R.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00233##  or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; or R.sup.10 and R.sup.11 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a (CO)—R.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, ##STR00234##  or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10a; R.sup.10a and R.sup.11a independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, S(O).sub.m—(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), (CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.10a and R.sup.11a independently of each other are C.sub.1-C.sub.20alkyl substituted by one or more halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)—(C.sub.1-C.sub.8alkyl), O(CO)—(C.sub.2-C.sub.4)alkenyl, O(CO)-phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2—(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl or C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sup.10a and R.sup.11a independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.10a and R.sup.11a independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); or R.sup.10a and R.sup.11a independently of each other are C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)—C.sub.1-C.sub.8alkyl or (CO)N(C.sub.1-C.sub.8alkyl).sub.2, phenyl or benzoyl; or R.sup.10a and R.sup.11a independently of each other are C.sub.1-C.sub.20alkanoyl, C.sub.3-C.sub.12alkenoyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; or R.sup.10a and R.sup.11a independently of each other are C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.10a and R.sup.11a independently of each other are C.sub.1-C.sub.20alkoxy, which is interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2; or R.sup.10a and R.sup.11a independently of each other are C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, CO(OC.sub.1-C.sub.8alkyl), (CO)—(C.sub.1-C.sub.8alkyl) or SO.sub.2—(C.sub.1-C.sub.8alkyl); or R.sup.10a and R.sup.11a together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or N(C.sub.1-C.sub.8alkyl), and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, NO.sub.2, halogen, C.sub.1-C.sub.4haloalkyl, CN, phenyl or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or N(C.sub.1-C.sub.8alkyl); R.sup.12 and R.sup.13 independently of each other are hydrogen, C.sub.1-C.sub.12alkyl optionally substituted by one or more halogen, phenyl, CN, —OH, —SH, C.sub.1-C.sub.4alkoxy, (CO)OH or (CO)O(C.sub.1-C.sub.4alkyl); or R.sup.12 and R.sup.13 are phenyl optionally substituted by one or more C.sub.1-C.sub.6alkyl, halogen, CN, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.12 and R.sup.13 are halogen, CN, OR.sup.4, SR.sup.9, SOR.sup.9, SO.sub.2R.sup.9 or NR.sup.10R.sup.11, wherein the substituents OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11 optionally form 5- or 6-membered rings via the radicals R.sup.4, R.sup.9, R.sup.10 and/or R.sup.11 with one of the carbon atoms of the phenyl, naphthyl, benzoyl or naphthoyl group or that of the substituent R.sup.3a; or R.sup.2 and R.sup.13 together are a group ##STR00235##  wherein R.sup.14, R.sup.15, R.sup.16 and R.sup.17 independently of one another are hydrogen, C.sub.1-C.sub.12alkyl optionally substituted by one or more halogen, phenyl, CN, —OH, —SH, C.sub.1-C.sub.4alkoxy, (CO)OH or (CO)O(C.sub.1-C.sub.4alkyl); or R.sup.14, R.sup.15, R.sup.16 and R.sup.17 are phenyl optionally substituted by one or more C.sub.1-C.sub.6alkyl, halogen, CN, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.14, R.sup.15, R.sup.16 and R.sup.17 are halogen, CN, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.12 and R.sup.13 together are a group ##STR00236##  wherein R.sup.18 and R.sup.19 independently of each other are hydrogen, C.sub.1-C.sub.12alkyl optionally substituted by one or more halogen, phenyl, CN, —OH, —SH, C.sub.1-C.sub.4-alkoxy, (CO)OH or (CO)O(C.sub.1-C.sub.4alkyl); or R.sup.18 and R.sup.19 are phenyl optionally substituted by one or more C.sub.1-C.sub.6alkyl, halogen, CN, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; M is a direct bond or a divalent linking group C.sub.1-C.sub.20alkylene or C.sub.1-C.sub.20alkylene substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or M is C.sub.1-C.sub.20alkylene interrupted by one or more O, S, NR.sup.10, CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—R.sup.3a, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or M is C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10 or COOR.sup.4; or M is C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, COOR.sup.4, (CO)—R.sup.3a or SO.sub.2—R.sup.3a; M′ is a direct bond or a divalent linking group selected from C.sub.1-C.sub.20alkylene or C.sub.1-C.sub.20alkylene substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or M′ is C.sub.1-C.sub.20alkylene interrupted by one or more O, S, NR.sup.10, CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—R.sup.3a, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or M′ is C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10 or COOR.sup.4; or M′ is C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, COOR.sup.4, (CO)—R.sup.3a or SO.sub.2—R.sup.3a; M″ is a direct bond or a divalent linking group selected from C.sub.1-C.sub.20alkylene or C.sub.1-C.sub.20alkylene substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or M″ is C.sub.1-C.sub.20alkylene interrupted by one or more O, S, NR.sup.10, CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—R.sup.3a, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or M″ is C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10 or COOR.sup.4; or M″ is C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, COOR.sup.4, (CO)—R.sup.3a or SO.sub.2—R.sup.3a; m is 1 or 2; Q is CO or a direct bond; and x, y and z independently of each other are an integer 1, 2, 3 or 4.

    23. The compound of the formula I, II, III or IV according to claim 22, wherein the compound is a compound of the formula Ia, IIa, IIIa or IVa: ##STR00237## wherein R.sup.1 to R.sup.8, R.sup.1′, R.sup.2′, R.sup.4′, M, M′ and M″ are defined as in claim 22.

    24. The compound of the formula I, II, III or IV according to claim 22, wherein the compound is a compound of the formula Ib, IIb, IIIb or IVb: ##STR00238## wherein R.sup.1 is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.20cycloalkyl, C.sub.2-C.sub.12alkenyl, wherein C.sub.3-C.sub.20cycloalkyl or C.sub.2-C.sub.12alkenyl is uninterrupted or interrupted by one or more O, S, CO, NR.sup.10 or COOR.sup.4; or R.sup.1 is C.sub.2-C.sub.20alkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO, SO.sub.2, phenylene, naphthylene or NR.sup.10, wherein the interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more halogen, C.sub.3-C.sub.8cycloalkyl, OH, SH, OR.sup.4, SR.sup.9, COOR.sup.4, O(CO)—R.sup.3a, CONR.sup.10R.sup.11, NR.sup.10R.sup.11, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; or R.sup.1 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl each of which is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl; R.sup.1′ is C.sub.1-C.sub.20alkylene, C.sub.1-C.sub.20alkylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or NR.sup.B, wherein the C.sub.1-C.sub.20alkylene and interrupted C.sub.1-C.sub.20alkylene is unsubstituted or substituted by halogen or OR.sup.4, R.sup.2 is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sup.4, SR.sup.9, COOR.sup.4CONR.sup.10R.sup.11, NR.sup.10R.sup.11, PO(OR.sup.3a).sub.2; (CO)—R.sup.3a, or R.sup.2 is C.sub.2-C.sub.20alkyl or C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6-cycloalkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO, SO.sub.2, phenylene, naphthylene or NR.sup.10; or R.sup.2 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl each of which is unsubstituted or substituted by one or more C.sub.1-C.sub.12alkyl, (CO)—R.sup.3a; R.sup.2′ is C.sub.1-C.sub.20alkylene, C.sub.1-C.sub.20alkylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or NR.sup.B, wherein the C.sub.1-C.sub.20alkylene and interrupted C.sub.1-C.sub.20alkylene is unsubstituted or substituted by halogen or OR.sup.4, R.sup.3 is hydrogen or C.sub.1-C.sub.20alkyl; or R.sup.3 is C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; R.sup.3a is hydrogen or C.sub.1-C.sub.20alkyl; or R.sup.3a is C.sub.1-C.sub.20alkyl interrupted by one or more O, S, NR.sup.10a CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—(C.sub.1-C.sub.8alkyl), COOR.sup.4a, CONR.sup.10aR.sup.11a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.4a, SR.sup.9a or NR.sup.10aR.sup.11a; or R.sup.3a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.4a, SR.sup.9a, NR.sup.10aR.sup.11a, COOR.sup.4a, (CO)—(C.sub.1-C.sub.8alkyl) or SO.sub.2—(C.sub.1-C.sub.4haloalkyl); R.sup.4 is hydrogen, (CO)—R.sup.3a, COOR.sup.4a, CONR.sup.10R.sup.11, S(O).sub.m—R.sup.3a or PO(OR.sup.3a).sub.2; R.sup.4′ is —(CO)—, —(CO)O—, —(CO)N—, —S(O).sub.m—, —PO(O).sub.2—, or —OP(O).sub.2; R.sup.4a is hydrogen, C.sub.1-C.sub.20alkyl, (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.4a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.4a is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)—C.sub.1-C.sub.8alkyl or (CO)N(C.sub.1-C.sub.8).sub.2, phenyl or benzoyl; R.sup.8 is hydrogen, C.sub.1-C.sub.20alkyl or C.sub.6-C.sub.20aryl; R.sup.9 is hydrogen or C.sub.1-C.sub.20alkyl; R.sup.9a is hydrogen or C.sub.1-C.sub.20alkyl; R.sup.10 and R.sup.11 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, S(O).sub.m—R.sup.3a, O(CO)—R.sup.3a(CO)—R.sup.3a or CONR.sup.10aR.sup.11a; R.sup.10a and R.sup.11a independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, S(O).sub.m—(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), (CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; M is a direct bond or a divalent linking group C.sub.1-C.sub.20alkylene or C.sub.1-C.sub.20alkylene substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; M′ is a direct bond or a divalent linking group selected from C.sub.1-C.sub.20alkylene or C.sub.1-C.sub.20alkylene substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; M″ is a direct bond or a divalent linking group selected from C.sub.1-C.sub.20alkylene or C.sub.1-C.sub.20alkylene substituted by one or more halogen, OR.sup.4, SR.sup.9, NR.sup.10R.sup.11, CN, COOR.sup.4, CONR.sup.10R.sup.11, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.10; or by one or more C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.4, SR.sup.9 or NR.sup.10R.sup.11; and m is 1 or 2.

    25. The compound of the formula I, II, III or IV according to claim 24, wherein the compound is a compound of the formula Ib, wherein R.sup.1 is C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.20cycloalkyl; or R.sup.1 is C.sub.2-C.sub.20alkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO, or SO.sub.2; or R.sup.1 is C.sub.6-C.sub.20aryl which is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl; R.sup.2 is C.sub.1-C.sub.20alkyl; or R.sup.2 is C.sub.2-C.sub.20alkyl or C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6-cycloalkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO or SO.sub.2; or R.sup.2 is C.sub.6-C.sub.20aryl which is unsubstituted or substituted by one or more C.sub.1-C.sub.12alkyl or (CO)—R.sup.3a; R.sup.3 is C.sub.1-C.sub.20alkyl; R.sup.3a is C.sub.1-C.sub.20alkyl, C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl; R.sup.4 is (CO)—R.sup.3a, COOR.sup.4a, CONR.sup.10R.sup.11, S(O).sub.m—R.sup.3a or PO(OR.sup.3a).sub.2; R.sup.4a is C.sub.1-C.sub.20alkyl, C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl; R.sup.10 and R.sup.11 are C.sub.1-C.sub.20alkyl; and m is 1 or 2.

    26. The Compound of the formula I, II, III or IV according to claim 22, wherein (i) more than 50% of the C═N double bonds present in oxime ester groups in the molecule are in Z configuration; or (ii) more than 50% of the C═N double bonds present in oxime ester groups in the molecule are in E configuration.

    27. A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable compound and (b) as photoinitiator, at least one compound of the formula I, II, III or IV as defined in claim 22.

    28. The photopolymerizable composition according to claim 27, wherein the component (a) is a resin obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of an epoxy resin and an unsaturated monocarboxylic acid.

    29. The photopolymerizable composition according to claim 27, additionally to the photoinitiator (b) comprising at least one further photoinitiator (c), and/or other additives (d).

    30. The photopolymerizable composition according to claim 27 as further additive (d) comprising a pigment, or a mixture of pigments, or a dye, or a mixture of dyes, or a mixture of one or more pigments with one or more dyes.

    31. The photopolymerizable composition according to claim 30 as further additive (d) comprising a dispersant or a mixture of dispersants.

    32. The photopolymerizable composition according to claim 27, comprising 0.05 to 25% by weight of the photoinitiator (b), or the photoinitiators (b) and (c), based on the weight of the composition.

    33. The photopolymerizable composition according to claim 27 as further additive (d) comprising a photosensitizer a compound selected from the group consisting of benzophenone, benzophenone derivatives, thioxanthone, thioxanthone derivatives, anthraquinone, anthraquinone derivatives, coumarin, and coumarine derivatives.

    34. The photopolymerizable composition according to claim 27 additionally comprising a binder polymer (e), in particular a copolymer of methacrylate and methacrylic acid.

    35. A process for the preparation of a compound of the formula I, II, III or IV according to claim 22 by reacting the corresponding oxime compound with an acyl halide of the formula I′ or an anhydride of the formula I″ ##STR00239## wherein Hal is a halogen, in particular Cl, and R.sup.3 is as defined in claim 22, in the presence of a base or a mixture of bases.

    36. A process for the photopolymerization of compounds containing ethylenically unsaturated double bonds, which comprises irradiating a composition according to claim 27 with electromagnetic radiation in the range from 150 to 600 nm, or with electron beam or with X-rays.

    37. The process according to claim 36 further comprising producing pigmented and nonpigmented paints and varnishes, powder coatings, printing inks, printing plates, adhesives, pressure sensitive adhesives, dental compositions, gel coats, photoresists for electronics, electroplating resists, etch resists, both liquid and dry films, solder resists, resists to manufacture color filters for a variety of display applications, resists to generate structures in the manufacturing processes of plasma-display panels, electroluminescence displays and LCD, spacers for LCD, for holographic data storage (HDS), as composition for encapsulating electrical and electronic components, for producing magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etch masks, colour proofing systems, glass fibre cable coatings, screen printing stencils, for producing three-dimensional objects by means of stereolithography, as image recording material, for holographic recordings, microelectronic circuits, decolorizing materials, decolorizing materials for image recording materials, for image recording materials using microcapsules, as a photoresist material for a UV and visible laser direct imaging system, as a photoresist material used for forming dielectric layers in a sequential build-up layer of a printed circuit board.

    38. A coated substrate which is coated on at least one surface with the composition according to claim 27.

    39. A process for the photographic production of relief images, comprising subjection the coated substrate according to claim 38 to imagewise exposure and removing the unexposed portions with a developer.

    40. A color filter prepared by providing red, green and blue picture elements and a black matrix, all comprising a photosensitive resin and a pigment on a transparent substrate and providing a transparent electrode either on the surface of the substrate or on the surface of the color filter layer, wherein said photosensitive resin comprises a polyfunctional acrylate monomer, an organic polymer binder and the photopolymerization initiator of formula I, II, III or IV as defined in claim 22.

    41. A method comprising utilizing the compound of the formula I, II, III or IV as defined in claim 22 for the photopolymerization of a composition comprising at least one ethylenically unsaturated photopolymerizable compound.

    42. A compound of formula IA, IIA, IIIA or IVA, ##STR00240## wherein R.sup.1, R.sup.2, R.sup.4 to R.sup.8, R.sup.1′, R.sup.2, R.sup.4′, M, M′ and M″ are defined as in claim 22.

    Description

    SUBSTANCE EXAMPLES

    Example 1: Preparation of OE1

    [0305] ##STR00046##

    [0306] OE1 is prepared according to the following scheme:

    ##STR00047## ##STR00048##

    Preparation of IM1-1

    [0307] To a solution of 9-ethylcarbazole (3.0 g, 15.4 mmol) and Aluminum Chloride (2.25 g, 16.9 mmol) in DCM (100 ml) was added 4-Methoxybenzoyl chloride (2.62 g, 15.4 mmol) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added Aluminum Chloride (2.25 g, 16.9 mmol) and 4-Methylvaleryl Chloride (2.1 ml, 15.4 mmol), and the mixture was stirred for 30 min. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (3.6 g, 55%).

    Preparation of IM1-2

    [0308] To a solution of IM1-1 (3.6 g, 8.4 mmol) in Toluene (100 ml) was added Aluminum Chloride (3.38 g, 25.3 mmol), and the mixture was stirred for 2 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (3.0 g, 87%).

    Preparation of IM1-3

    [0309] To a solution of IM1-2 (0.50 g, 1.2 mmol) and TEA (0.17 ml, 1.21 mmol) in DCM (100 ml) was added Benzoyl Chloride (0.14 ml, 1.2 mmol) at 0° C., and the mixture was stirred for 30 min at room temperature (rt). The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (0.59 g, 94%).

    Preparation of IM1-4

    [0310] To a solution of IM1-3 (0.59 g, 1.14 mmol) in DMF (10 ml) was added conc. HCl (0.10 ml, 1.2 mmol) and Amyl Nitrite (0.23 ml, 1.7 mmol) at 0° C., and the mixture was stirred overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (0.32 g, 51%).

    Preparation of OE1

    [0311] To a solution of the IM1-4 (0.32 g, 0.59 mmol) in DCM (30 ml) was added TEA (0.09 ml, 0.64 mmol) and AcCl (0.05 ml, 0.70 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. Silica gel was added to the solution. The yellow silica gel was removed by cotton filtration, and washed with DCM. The solvent was removed under reduced pressure to give the product (0.17 g, 49%).

    Example 2: Preparation of OE2

    [0312] ##STR00049##

    [0313] OE2 is prepared according to the following scheme:

    ##STR00050##

    Preparation of IM2-1

    [0314] To a solution of 9-ethylcarbazole (3.0 g, 15.4 mmol) and Aluminum Chloride (2.25 g, 16.9 mmol) in DCM (100 ml) was added 4-Methoxybenzoyl chloride (2.62 g, 15.4 mmol) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added Aluminum Chloride (2.25 g, 16.9 mmol) and 4-Methylvaleryl Chloride (2.1 ml, 15.4 mmol), and the mixture was stirred for 30 min. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (3.6 g, 55%).

    Preparation of IM2-2

    [0315] To a solution of IM2-1 (3.6 g, 8.4 mmol) in Toluene (100 ml) was added Aluminum Chloride (3.38 g, 25.3 mmol), and the mixture was stirred for 2 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (3.0 g, 87%).

    Preparation of IM2-3

    [0316] To a solution of IM2-2 (0.50 g, 1.21 mmol) in DMF (10 ml) was added conc. HCl (0.15 ml, 1.8 mmol) and Amyl Nitrite (0.24 ml, 1.8 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (0.35 g, 65%).

    Preparation of OE2

    [0317] To a solution of the IM2-3 (0.35 g, 0.79 mmol) in DCM (20 ml) was added TEA (0.23 ml, 1.6 mmol) and AcCl (0.12 ml, 1.6 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. Silica gel was added to the solution. The yellow silica gel was removed by cotton filtration, and washed with DCM. The solvent was removed under reduced pressure to give the product (0.39 g, 74%).

    Example 3: Preparation of OE3

    [0318] ##STR00051##

    [0319] OE3 is prepared as the following scheme:

    ##STR00052##

    Preparation of IM3-1

    [0320] To 10.05 g of 9-ethylcarbazole and 6.87 g of aluminum chloride in chlorobenzene (100 ml) was added 8.80 g of 4-methoxybenzoyl chloride and stirred at room temperature (rt) for 2 h under N.sub.2 flow condition. To the reaction mixture was added 8.38 g of n-octanoyl chloride and 13.76 g of aluminum chloride and stirred at rt for 16 h under N.sub.2 flow condition, then heated at 100° C. for 1 h. The reaction mixture was poured into ice-water, and the precipitate was collected by filtration and washed with mixture of hexane and dichloromethane (DCM). The resulting solid was dried in vacuo to give 25.81 g of IM3-1 as beige solid.

    Preparation of IM3-2

    [0321] To 3.25 g of IM3-1 was added mixture of DMF (40 ml) and hydrochloric acid (10 ml) at rt. Then, 1.25 g of amyl nitrite was added and stirred for 20 h. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 2.55 g of IM3-2 as orange resin.

    Preparation of OE3

    [0322] To 2.55 of IM3-2 and 3.00 g of acetyl chloride in tetrahydrofuran (20 ml) was added 3.96 g of triethylamine at 0° C., then stirred at room temperature for 3 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 1.33 g of OE3 as yellow resin.

    Example 4: Preparation of OE4

    [0323] ##STR00053##

    [0324] OE4 is prepared as the following scheme:

    ##STR00054##

    Preparation of IM4-1

    [0325] To 9.80 g of 9-ethylcarbazole and 6.70 g of aluminum chloride in chlorobenzene (100 ml) was added 8.64 g of 4-methoxybenzoyl chloride and stirred at rt for 4 h under N.sub.2 flow condition. To the reaction mixture was added 5.36 g of n-butyryl chloride and 13.87 g of aluminum chloride and stirred at rt for 1 h under N.sub.2 flow condition, then heated at 100° C. for 3 h. The reaction mixture was poured into ice-water and the precipitate was collected by filtration and dried in vacuo. The resulting solid was washed with mixture of hexane and DCM, giving 21.74 g of IM4-1 as beige solid.

    Preparation of IM4-2

    [0326] To 20.69 g of IM4-1 was added mixture of DMF (100 ml), tetrahydrofuran (200 ml) and hydrochloric acid (30 ml) at rt. Then, 7.45 g of amyl nitrite was added and stirred for 4 h. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 19.81 g of IM4-2 as yellow powder.

    Preparation of OE4

    [0327] To 19.81 of IM4-2 and 8.11 g of acetyl chloride in tetrahydrofuran (200 ml) was added 1046 g of triethylamine at 0° C., then stirred at room temperature for 15 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 4.96 g of OE4 as yellow resin.

    Example 5: Preparation of OE5

    [0328] ##STR00055##

    [0329] OE5 is prepared according to the following scheme:

    ##STR00056##

    Preparation of IM5-1

    [0330] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (200 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol) and Hexanoyl Chloride (6.89 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and dried to give the product (19.5 g, 92%).

    Preparation of IM5-2

    [0331] To a solution of IM5-1 (6.00 g, 14.5 mmol) in DMF (50 ml) was added conc. HCl (1.8 ml, 22 mmol) and Amyl Nitrite (2.9 ml, 22 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and dried to give the product (5.3 g, 83%).

    Preparation of OE5

    [0332] To a solution of the IM5-2 (5.3 g, 12 mmol) in DCM (120 ml) was added TEA (3.6 ml, 25 mmol) and AcCl (1.8 ml, 25 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (3.56 g, 56%).

    Example 6: Preparation of OE6

    [0333] ##STR00057##

    [0334] OE6 is prepared according to the following scheme:

    ##STR00058##

    Preparation of IM6-1

    [0335] To a solution of 9-ethylcarbazole (6.00 g, 30.7 mmol) and Aluminum Chloride (4.51 g, 33.8 mmol) in Chlorobenzene (300 ml) was added 4-Methoxybenzoyl chloride (5.24 g, 30.7 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (4.51 g, 33.8 mmol) and Propionyl Chloride (2.84 g, 30.7 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (4.51 g, 33.8 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The precipitated solid was collected by filtration and washed with water to give the product (10.1 g, 89%).

    Preparation of IM6-2

    [0336] To a solution of IM6-1 (6.00 g, 16.2 mmol) in DMF (50 ml) was added conc. HCl (2.0 ml, 24 mmol) and Amyl Nitrite (3.2 ml, 24 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and DCM/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with DCM/Hexane to give the product (5.16 g, 80%).

    Preparation of OE6

    [0337] To a solution of the IM6-2 (5.16 g, 12.9 mmol) in DCM (130 ml) was added TEA (3.8 ml, 27 mmol) and AcCl (1.9 ml, 27 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (3.5 g, 56%).

    Example 7: Preparation of OE7

    [0338] ##STR00059##

    [0339] OE7 is prepared according to the following scheme:

    ##STR00060##

    Preparation of IM7-1

    [0340] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (300 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 56.8 mmol) and Valeryl Chloride (6.17 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 56.8 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (14.0 g, 68%).

    Preparation of IM7-2

    [0341] To a solution of IM7-1 (6.00 g, 15.0 mmol) in DMF (80 ml) was added conc. HCl (1.9 ml, 22 mmol) and Amyl Nitrite (3.0 ml, 22 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and DCM/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with DCM/Hexane to give the product (5.9 g, 90%).

    Preparation of OE7

    [0342] To a solution of the IM7-2 (5.8 g, 13 mmol) in DCM (130 ml) was added TEA (4.0 ml, 28 mmol) and AcCl (2.0 ml, 28 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (3.8 g, 55%).

    Example 8: Preparation of OE8

    [0343] ##STR00061##

    OE8 is prepared as the following scheme:

    ##STR00062##

    Preparation of IM8-1

    [0344] To 10.04 g of 9-ethylcarbazole and 6.88 g of aluminum chloride in chlorobenzene (100 ml) was added 8.77 g of 4-methoxybenzoyl chloride and stirred at rt for 1 h under N.sub.2 flow condition. To the reaction mixture was added 9.09 g of n-nonanoyl chloride and 14.00 g of aluminum chloride and stirred at rt for 2 h under N.sub.2 flow condition, then heated at 100° C. for 4 h. The reaction mixture was poured into ice-water and the precipitate was collected by filtration and dried in vacuo. The resulting solid was washed with mixture of hexane and DCM, giving 45.49 g of IM8-1 as beige solid.

    Preparation of IM8-2

    [0345] To 6.02 g of IM8-1 was added mixture of DMF (50 ml), tetrahydrofuran (50 ml) and hydrochloric acid (10 ml) at rt. Then, 1.67 g of amyl nitrite was added and stirred for 4 h. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 1.81 g of IM8-2 as brown resin.

    Preparation of OE8

    [0346] To 5.96 of IM8-2 and 2.10 g of acetyl chloride in tetrahydrofuran (100 ml) was added 2.65 g of triethylamine at 0° C., then stirred at room temperature for 1 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 4.37 of OE8 as off-white powder. The E:Z ratio was found to be 93:7.

    Example 9: Preparation of OE9

    [0347] ##STR00063##

    [0348] OE9 is prepared according to the following scheme:

    ##STR00064##

    Preparation of IM9-1

    [0349] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (300 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 56.8 mmol) and Heptanoyl Chloride (7.61 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 56.8 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and DCM/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with DCM/Hexane to give the product (17.8 g, 82%).

    Preparation of IM9-2

    [0350] To a solution of IM9-1 (4.00 g, 9.36 mmol) and TEA (1.4 ml, 9.9 mmol) in DCM (100 ml) was added Heptanoyl Chloride (1.5 ml, 9.9 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and DCM/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with DCM/Hexane to give the product (3.85 g, 76%).

    Preparation of IM9-3

    [0351] To a solution of IM9-2 (3.85 g, 7.13 mmol) in DMF (24 ml) was added conc. HCl (0.65 ml, 7.8 mmol) and Amyl Nitrite (1.05 ml, 7.8 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (2.4 g, 59%).

    Preparation of OE9

    [0352] To a solution of the IM9-3 (2.4 g, 4.2 mmol) in DCM (40 ml) was added TEA (0.62 ml, 4.4 mmol) and AcCl (0.32 ml, 4.4 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Diethyl ether/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Diethyl ether/Hexane to give the product (1.9 g, 75%).

    Example 10: Preparation of OE10

    [0353] ##STR00065##

    [0354] OE10 is prepared according to the following scheme:

    ##STR00066##

    Preparation of IM10-1

    [0355] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (300 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 56.8 mmol) and Valeryl Chloride (6.17 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 56.8 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (14.0 g, 68%).

    Preparation of IM10-2

    [0356] To a solution of IM10-1 (4.00 g, 9.36 mmol) and TEA (1.4 ml, 9.9 mmol) in DCM (100 ml) was added Valeryl Chloride (1.2 ml, 10 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Diethyl ether/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Diethyl ether/Hexane to give the product (4.40 g, 91%).

    Preparation of IM10-3

    [0357] To a solution of IM10-2 (4.40 g, 9.10 mmol) in DMF (30 ml) was added conc. HCl (0.83 ml, 10 mmol) and Amyl Nitrite (1.3 ml, 10 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (2.6 g, 56%).

    Preparation of OE10

    [0358] To a solution of the IM10-3 (2.6 g, 5.1 mmol) in DCM (50 ml) was added TEA (0.75 ml, 5.3 mmol) and AcCl (0.38 ml, 5.3 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (2.4 g, 86%).

    Example 11: Preparation of OE11

    [0359] ##STR00067##

    [0360] OE11 is prepared according to the following scheme:

    ##STR00068##

    Preparation of/IM11-1

    [0361] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (200 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol) and Hexanoyl Chloride (6.89 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and dried to give the product (19.5 g, 92%).

    Preparation of IM11-2

    [0362] To a solution of IM11-2 (7.00 g, 16.9 mmol) and TEA (2.5 ml, 18 mmol) in DCM (160 ml) was added Hexanoyl Chloride (2.4 ml, 18 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Diethyl ether/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Diethyl ether/Hexane to give the product (6.32 g, 73%).

    Preparation of IM11-3

    [0363] To a solution of IM11-2 (4.00 g, 7.81 mmol) in DMF (40 ml) was added conc. HCl (0.98 ml, 12 mmol) and Amyl Nitrite (1.6 ml, 12 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (2.91 g, 69%).

    Preparation of OE11

    [0364] To a solution of the IM11-3 (2.91 g, 5.38 mmol) in DCM (50 ml) was added TEA (0.79 ml, 5.6 mmol) and AcCl (0.40 ml, 5.6 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (2.44 g, 78%).

    Example 12: Preparation of OE12

    [0365] ##STR00069##

    [0366] OE12 is prepared according to the following scheme:

    ##STR00070##

    Preparation of IM12-1

    [0367] To a solution of 9-ethylcarbazole (5.00 g, 25.6 mmol) and Aluminum Chloride (3.75 g, 28.1 mmol) in DCM (250 ml) was added 2-Methoxybenzoyl chloride (4.37 g, 25.6 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (3.75 g, 28.1 mmol) and Octanoyl Chloride (4.16 g, 25.6 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.5 g, 56 mmol), and the mixture was stirred for 2 h at the reflux temperature. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and dried to give the product (8.6 g, 81%).

    Preparation of IM12-2

    [0368] To a solution of IM12-1 (0.50 g, 1.21 mmol) and TEA (0.18 ml, 1.3 mmol) in DCM (100 ml) was added Benzenesulfonyl chloride (0.16 ml, 1.3 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (0.57 g, 81%).

    Preparation of IM12-3

    [0369] To a solution of IM12-2 (0.57 g, 0.98 mmol) in DMF (30 ml) was added conc. HCl (0.12 ml, 1.4 mmol) and Amyl Nitrite (0.20 ml, 1.5 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (0.47 g, 79%).

    Preparation of OE12

    [0370] To a solution of the IM12-3 (0.47 g, 0.77 mmol) in DCM (100 ml) was added TEA (0.11 ml, 0.78 mmol) and AcCl (0.06 ml, 0.84 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. Silica gel was added to the solution. The yellow silica gel was removed by cotton filtration, and washed with DCM. The solvent was removed under reduced pressure to give the product (0.39 g, 78%).

    Example 13: Preparation of OE13

    [0371] ##STR00071##

    [0372] OE13 is prepared according to the following scheme:

    ##STR00072##

    Preparation of IM13-1

    [0373] To a solution of 9-ethylcarbazole (5.00 g, 25.6 mmol) and Aluminum Chloride (3.75 g, 28.1 mmol) in DCM (250 ml) was added 2-Methoxybenzoyl chloride (4.37 g, 25.6 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (3.75 g, 28.1 mmol) and Octanoyl Chloride (4.16 g, 25.6 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.5 g, 56 mmol), and the mixture was stirred for 2 h at the reflux temperature. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and dried to give the product (8.6 g, 81%).

    Preparation of IM13-2

    [0374] To a solution of IM13-1 (0.55 g, 1.33 mmol) in DMF (20 ml) was added conc. HCl (0.16 ml, 1.9 mmol) and Amyl Nitrite (0.26 ml, 1.9 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (0.42 g, 67%).

    Preparation of OE13

    [0375] To a solution of the IM13-2 (0.42 g, 0.89 mmol) in DCM (100 ml) was added TEA (0.26 ml, 1.8 mmol) and AcCl (0.13 ml, 1.8 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. Silica gel was added to the solution. The yellow silica gel was removed by cotton filtration, and washed with DCM. The solvent was removed under reduced pressure to give the product (0.41 g, 83%).

    Example 14: Preparation of OE14

    [0376] ##STR00073##

    [0377] OE14 is prepared according to the following scheme:

    ##STR00074##

    Preparation of IM14-1

    [0378] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (200 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol) and Hexanoyl Chloride (6.89 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and dried to give the product (19.5 g, 92%).

    Preparation of IM14-2

    [0379] To a solution of IM14-1 (4.00 g, 9.67 mmol) and TEA (1.4 ml, 10 mmol) in DCM (100 ml) was added Isobutyryl Chloride (1.1 ml, 10 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (3.27 g, 70%).

    Preparation of IM14-3

    [0380] To a solution of IM14-2 (3.27 g, 6.77 mmol) in DMF (30 ml) was added conc. HCl (0.85 ml, 10 mmol) and Amyl Nitrite (1.35 ml, 10 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (2.60 g, 75%).

    Preparation of OE14

    [0381] To a solution of the IM14-3 (2.60 g, 5.07 mmol) in DCM (50 ml) was added TEA (0.75 ml, 5.3 mmol) and AcCl (0.38 ml, 5.3 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (1.90 g, 68%).

    Example 15: Preparation of OE15

    [0382] ##STR00075##

    [0383] OE15 is prepared according to the following scheme:

    ##STR00076##

    Preparation of IM15-1

    [0384] To a solution of 9-ethylcarbazole (30.0 g, 153 mmol) and Aluminum Chloride (21.5 g, 161 mmol) in DCM (750 ml) was added 4-Methoxybenzoyl chloride (4.37 g, 25.6 mmol) at 0° C., and the mixture was stirred for 1 h. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Diethyl ether/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Diethyl ether/Hexane to give the product (43.2 g, 86%).

    Preparation of IM15-2

    [0385] To a solution of IM15-1 (4.00 g, 12.1 mmol) and Aluminum Chloride (4.84 g, 36.3 mmol) in Chlorobenzene (120 ml) was added Ethyl Glutaryl Chloride (1.9 ml, 12.1 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (1.61 g, 12 mmol), and the mixture was stirred for 1 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and DCM/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with DCM/Hexane to give the product (4.81 g, 87%).

    Preparation of IM15-3

    [0386] To a solution of IM15-2 (4.81 g, 10.5 mmol) in DMF (40 ml) was added conc. HCl (1.1 ml, 13 mmol) and Amyl Nitrite (1.7 ml, 13 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Diethyl ether/Hexane to give the product (3.54 g, 69%).

    Preparation of OE15

    [0387] To a solution of the IM15-3 (3.54 g, 7.28 mmol) in DCM (70 ml) was added TEA (2.2 ml, 15 mmol) and AcCl (1.1 ml, 15 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Diethyl ether/Hexane to give the product (2.50 g, 60%).

    Example 16: Preparation of OE16

    [0388] ##STR00077##

    [0389] OE16 is prepared according to the procedure described for OE17 below using hexanoyl chloride in place of heptanoyl chloride.

    Example 17: Preparation of OE17

    [0390] ##STR00078##

    [0391] OE17 is prepare according to the to the following scheme:

    ##STR00079##

    Preparation of IM17-1

    [0392] To a solution of Carbazole (50.2 g, 300 mmol) in DMA (150 ml) was added 2-Ethylhexyl Bromide (77.6 g, 450 mmol), KOH (25.3 g, 450 mmol) and Tetrabutylammonium Iodide (5.54 g, 15 mmol). The reaction mixture was stirred for overnight at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was removed by filtration and the solvent was removed under reduced pressure to give the product (75.0 g, 90%).

    Preparation of IM17-2

    [0393] To a solution of IM17-2 (27.9 g, 100 mmol) and Aluminum Chloride (14.0 g, 105 mmol) in Chlorobenzene (200 ml) was added 4-Methoxybenzoyl chloride (17 g, 100 mmol) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added Aluminum Chloride (28 g, 210 mmol) and Heptanoyl Chloride (15.5 g, 100 mmol), and the mixture was stirred for 1 h. To the reaction mixture was stirred for 2 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (34.3 g, 67%).

    Preparation of IM17-3

    [0394] To a solution of IM17-2 (10.2 g, 20.0 mmol) in DMF (30 ml) was added Isopropyl alcohol (2.0 ml, 28.5 mmol), Sodium nitrite (1.66 g, 24.0 mmol) and 4 M HCl Dioxane (15 ml, 60 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TMBE/Toluene was added to the crude product. The precipitated solid was collected by filtration and washed with Toluene to give the product (5.3 g, 49%).

    Preparation of OE17

    [0395] To a solution of IM-17-3 (5.3 g, 9.7 mmol) in TBME (50 ml) was added TEA (3.2 ml, 23 mmol) and Acetic anhydride (2.1 ml, 22 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched by water. The mixture was extracted with TBME, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Heptane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Heptane to give the product (5.1 g, 84%).

    [0396] The product OE17 was obtained mainly in E configuration. Samples of pure E isomer and pure Z isomer were prepared using conventional silica gel chromatography (DCM/Acetone). The Z isomer of OE17 (OE17-Z) can be prepared according to the following scheme:

    ##STR00080##

    Preparation of IM17-2Z

    [0397] To a solution of IM17-1 (240.5 g, 470.0 mmol) in DMF (575 ml) was added Isopropyl alcohol (47 ml, 671 mmol), Sodium nitrite (45.4 g, 658 mmol) and 4 M HCl Dioxane (421 ml, 1.68 mol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was dissolved in 500 ml of toluene at 60° C. To the solution 10 ml of butyl acetate and 50 ml of heptane were added and cooled down, leading to precipitation. The solid was isolated by filtration and washed with heptane, which was (mainly) composed of E-isomer. The filtrate was purified by silica gel chromatography (DCM/Acetone) to give 5.76 g of IM17-2Z (Z isomer).

    Preparation of OE17-Z

    [0398] To a solution of IM-17-2Z (5.2 g, 9.7 mmol) in TBME (20 ml) was added TEA (2.25 g, 22 mmol) and Acetic anhydride (2.17 g, 21 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched by water. The mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography (DCM/Acetone) to give 3.28 g (54%) of OE17-Z (Z isomer) as a dark yellow resin.

    Example 18: Preparation of OE18

    [0399] ##STR00081##

    [0400] OE18 is prepared according to the following scheme:

    ##STR00082## ##STR00083##

    Preparation of IM18-1

    [0401] To a solution of Carbazole (50.2 g, 300 mmol) in DMA (150 ml) was added 2-Ethylhexyl Bromide (77.6 g, 450 mmol), KOH (25.3 g, 450 mmol) and Tetrabutylammonium Iodide (5.54 g, 15 mmol). The reaction mixture was stirred for overnight at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was removed by filtration and the solvent was removed under reduced pressure to give the product (75.0 g, 90%).

    Preparation of IM18-2

    [0402] To a solution of IM18-1 (23.8 g, 85.2 mmol) and Aluminum Chloride (11.9 g, 89.2 mmol) in DCM (400 ml) was added 4-Methoxybenzoyl chloride (14.5 g, 85.0 mmol) at 0° C., and the mixture was stirred for 30 min. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (27.4 g, 78%).

    Preparation of IM18-3

    [0403] To a solution IM18-2 (12.2 g, 29.5 mmol) and Aluminum Chloride (7.86 g, 59.0 mmol) in Chlorobenzene (200 ml) was added Octanoyl chloride (5.1 ml, 29 mmol) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added Aluminum Chloride (3.93 g, 29.5 mmol), and the mixture was stirred for 1 h at 100° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (8.96 g, 58%).

    Preparation of IM18-4

    [0404] To a solution of IM18-3 (8.96 g, 17.0 mmol) in DMF (45 ml) was added conc. HCl (2.1 ml, 25 mmol) and Amyl Nitrite (3.4 ml, 25 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (6.27 g, 67%).

    Preparation of OE18

    [0405] To a solution of the IM18-4 (6.27 g, 11.3 mmol) in DCM (56 ml) was added TEA (3.3 ml, 23 mmol) and AcCl (1.7 ml, 23 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Diethyl ether/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Hexane to give the product (5.29 g, 73%).

    Example 19: Preparation of OE19

    [0406] ##STR00084##

    [0407] OE19 is prepared as the following scheme:

    ##STR00085##

    Preparation of IM19-1

    [0408] To 7.81 g of IM14-1 and 2.16 g of ethyl chloroformate in tetrahydrofuran (50 ml), 2.11 g of triethylamine was added at 0° C. and stirred for 4 h. The organic layer was extracted with TBME and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was reprecipitated from TBME/hexane to give 8.44 g of IM19-1 as pale orange solid.

    Preparation of IM19-2

    [0409] To 8.44 g of IM19-1 was added mixture of DMF (160 ml), tetrahydrofuran (110 ml) and hydrochloric acid (60 ml) at 0° C. Then, 4.62 g of amyl nitrite was added and stirred for 4 h at rt. The organic layer was extracted with TBME and washed with brine, then, dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 7.6 g of IM19-2 as brown resin.

    Preparation of OE19

    [0410] To 7.6 of IM19-2 and 4.96 g of acetyl chloride in tetrahydrofuran (80 ml) was added 6.4 g of triethylamine at 0° C., then stirred at rt for 15 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane/DCM/acetone (90:10:0 to 0:98:2 v/v/v) as eluent to give 1.02 g of OE19 as pale yellow solid.

    Example 20: Preparation of OE20

    [0411] ##STR00086##

    [0412] OE20 is prepared as the following scheme:

    ##STR00087##

    Preparation of IM20-1

    [0413] To 0.43 g of IM9-1 and 0.11 g of ethyl chloroformate in tetrahydrofuran (10 ml), 0.12 g of triethylamine was added at 0° C. and stirred for 4 h. The organic layer was extracted with TBME and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was washed with TBME/hexane to give 0.50 g of IM20-1 as orange powder.

    Preparation of IM20-2

    [0414] To 0.50 g of IM20-1 was added mixture of DMF (3 ml), tetrahydrofuran (3 ml) and hydrochloric acid (5 ml) at 0° C. Then, 0.32 g of amyl nitrite was added and stirred for 4 h at rt. The organic layer was extracted with TBME and washed with brine, then, dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 80:20 v/v) as eluent to give 0.34 g of IM20-2 as orange resin.

    Preparation of OE20

    [0415] To 0.34 of IM20-2 and 0.14 g of acetyl chloride in tetrahydrofuran (10 ml) was added 0.24 g of triethylamine at 0° C., then stirred at rt for 2 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane/DCM/acetone (90:10:0 to 0:99:1 v/v/v) as eluent to give 0.30 of OE20 as yellow resin.

    Example 21: Preparation of OE21

    [0416] ##STR00088##

    [0417] OE21 is prepared as the following scheme:

    ##STR00089##

    Preparation of IM21-1

    [0418] To 4.57 g of IM3-1 and 1.14 g of ethyl chloroformate in tetrahydrofuran (40 ml), 1.14 g of triethylamine was added at 0° C. and stirred for 4 h. The organic layer was extracted with TBME and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was washed with TBME/hexane to give 4.88 g of IM21-1 as off-white powder.

    Preparation of IM21-2

    [0419] To 4.88 g of IM21-1 was added mixture of DMF (100 ml), tetrahydrofuran (100 ml) and hydrochloric acid (30 ml) at 0° C. Then, 2.53 g of amyl nitrite was added and stirred for 4 h at rt. The organic layer was extracted with TBME and washed with brine, then, dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 2.65 g of IM21-2 as yellow resin.

    Preparation of OE21

    [0420] To 2.65 of IM21-2 and 0.91 g of acetyl chloride in tetrahydrofuran (50 ml) was added 1.16 g of triethylamine at 0° C., then stirred at rt for 2 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 80:20 v/v) as eluent to give 2.01 of OE21 as yellow resin.

    Example 22: Preparation of OE22

    [0421] ##STR00090##

    [0422] OE22 is prepared according to the following scheme:

    ##STR00091##

    Preparation of IM22-1

    [0423] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (300 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol) and Valeryl Chloride (6.17 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (14.0 g, 68%).

    Preparation of IM22-2

    [0424] To a solution of IM22-1 (10.0 g, 25.0 mmol) and TEA (3.5 ml, 25 mmol) in DCM (300 ml) was added Propyl Chloroformate (2.8 ml, 25 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Hexane to give the product (11.2 g, 92%).

    Preparation of IM22-3

    [0425] To a solution of IM22-2 (11.2 g, 23.1 mmol) in DMF (100 ml) was added conc. HCl (2.9 ml, 35 mmol) and Amyl Nitrite (4.6 ml, 35 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (9.00 g, 76%).

    Preparation of OE22

    [0426] To a solution of the IM22-3 (9.00 g, 17.5 mmol) in DCM (80 ml) was added TEA (2.5 ml, 18 mmol) and AcCl (1.25 ml, 18 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. Silica gel was added to the solution. The yellow silica gel was removed by cotton filtration, and washed with DCM. The solvent was removed under reduced pressure to give the product (5.96 g, 61%).

    Example 23: Preparation of OE23

    [0427] ##STR00092##

    [0428] OE23 is prepared according to the procedure described for OE22 above using hexanoyl chloride in place of valeryl chloride.

    Example 24: Preparation of OE24

    [0429] ##STR00093##

    [0430] OE24 is prepared according to the following scheme:

    ##STR00094##

    Preparation of IM24-1

    [0431] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (300 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol) and Heptanoyl Chloride (7.61 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with DCM/Hexane to give the product (17.8 g, 82%).

    Preparation of IM24-2

    [0432] To a solution of IM24-1 (6.27 g, 14.7 mmol) and TEA (2.2 ml, 16 mmol) in DCM (70 ml) was added Propyl Chloroformate (2.2 ml, 15 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Hexane to give the product (6.45 g, 85%).

    Preparation of IM24-3

    [0433] To a solution of IM24-2 (6.45 g, 12.6 mmol) in DMF (120 ml) was added conc. HCl (1.6 ml, 19 mmol) and Amyl Nitrite (2.5 ml, 19 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Hexane to give the product (4.40 g, 64%).

    Preparation of OE24

    [0434] To a solution of the IM24-3 (4.40 g, 8.10 mmol) in DCM (80 ml) was added TEA (1.2 ml, 8.5 mmol) and AcCl (0.61 ml, 8.5 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (2.60 g, 55%).

    Example 25: Preparation of OE25

    [0435] ##STR00095##

    [0436] OE25 is prepared as the following scheme:

    ##STR00096##

    Preparation of IM25-1

    [0437] To 4.29 g of IM14-1 and 1.49 g of butyl chloroformate in tetrahydrofuran (30 ml), 1.21 g of triethylamine was added at 0° C. and stirred for 4 h. The organic layer was extracted with TBME and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was washed with TBME/hexane to give 4.50 g of IM25-1 as off-white powder.

    Preparation of IM25-2

    [0438] To 4.47 g of IM25-2 was added mixture of DMF (130 ml), tetrahydrofuran (40 ml) and hydrochloric acid (30 ml) at 0° C. Then, 2.49 g of amyl nitrite was added and stirred for 4 h at rt. The organic layer was extracted with TBME and washed with brine, then, dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 3.20 g of IM25-3 as yellow resin.

    Preparation of OE25

    [0439] To 3.20 of IM25-2 and 1.30 g of acetyl chloride in tetrahydrofuran (50 ml) was added 1.78 g of triethylamine at 0° C., then stirred at rt for 2 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 90:10 v/v) as eluent to give 2.21 of OE25 as off-white powder.

    Example 26: Preparation of OE26

    [0440] ##STR00097##

    [0441] OE26 is prepared as the following scheme:

    ##STR00098##

    Preparation of IM26-1

    [0442] To 4.36 g of IM9-1 and 1.41 g of butyl chloroformate in tetrahydrofuran (50 ml), 1.06 g of triethylamine was added at 0° C. and stirred for 4 h. The organic layer was extracted with TBME and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was washed with TBME/hexane to give 4.69 g of IM26-1 as off-white powder.

    Preparation of IM26-2

    [0443] To 4.69 g of IM26-1 was added mixture of DMF (40 ml), tetrahydrofuran (40 ml) and hydrochloric acid (30 ml) at 0° C. Then, 2.02 g of amyl nitrite was added and stirred for 4 h at rt. The organic layer was extracted with TBME and washed with brine, then, dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 80:20 v/v) as eluent to give 2.35 g of IM26-2 as yellow resin.

    Preparation of OE26

    [0444] To 2.35 of IM26-2 and 0.31 g of acetyl chloride in tetrahydrofuran (40 ml) was added 0.41 g of triethylamine at 0° C., then stirred at rt for 2 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 80:20 v/v) as eluent to give 1.17 of OE26 as off-white powder.

    Example 27: Preparation of OE27

    [0445] ##STR00099##

    [0446] OE27 is prepared according to the following scheme:

    ##STR00100##

    Preparation of IM27-1

    [0447] To a solution of 9-ethylcarbazole (10.0 g, 51.2 mmol) and Aluminum Chloride (7.57 g, 56.8 mmol) in Chlorobenzene (200 ml) was added 4-Methoxybenzoyl chloride (8.74 g, 51.2 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol) and Hexanoyl Chloride (6.89 g, 51.2 mmol), and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (7.57 g, 51.2 mmol), and the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and Hexane was added to the crude product. The precipitated solid was collected by filtration and dried to give the product (19.5 g, 92%).

    Preparation of IM27-2

    [0448] To a solution of IM24-1 (4.30 g, 10.4 mmol) and TEA (1.7 ml, 12 mmol) in THF (30 ml) was added Isobutyl Chloroformate (1.4 ml, 10.7 mmol) at 0° C., and the mixture was stirred for 15 min at rt. The reaction mixture was quenched with water. The reaction mixture was extracted with TBME, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with Hexane to give the product (4.68 g, 88%).

    Preparation of IM27-3

    [0449] To a solution of IM27-2 (4.63 g, 9.01 mmol) in DMF (22 ml) was added conc. HCl (1.1 ml, 13 mmol) and Amyl Nitrite (1.8 ml, 13 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (2.83 g, 58%).

    Preparation of OE27

    [0450] To a solution of the IM27-3 (2.83 g, 5.22 mmol) in DCM (26 ml) was added TEA (0.77 ml, 5.5 mmol) and AcCl (0.39 ml, 5.5 mmol) at 0° C., and the mixture was stirred for 15 min. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and TBME/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with TBME/Hexane to give the product (2.72 g, 89%).

    Example 28: Preparation of OE28

    [0451] ##STR00101##

    [0452] OE28 is prepared according to the following scheme:

    ##STR00102##

    Preparation of IM28-1

    [0453] To 10.50 g of IM17-2 and 2.79 g of diethylcarbamoyl chloride in tetrahydrofuran (80 ml), 4.44 g of potassium carbonate and pyridine (3 ml) was added and stirred at 70° C. for 4 h. The organic layer was extracted with TBME and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 50:50 v/v) as eluent to give 7.36 g of IM28-1 as yellow resin.

    Preparation of IM28-2

    [0454] To 7.36 g of IM28-1 was added mixture of DMF (200 ml), tetrahydrofuran (150 ml) and hydrochloric acid (40 ml) at 0° C. Then, 4.91 g of amyl nitrite was added and stirred for 4 h at rt. The organic layer was extracted with TBME and washed with brine, then, dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 80:20 v/v) as eluent to give 1.03 g of IM28-2 as yellow oil.

    Preparation of OE28

    [0455] To 1.03 of IM28-2 and 0.77 g of acetyl chloride in tetrahydrofuran (30 ml) was added 1.02 g of triethylamine at 0° C., then stirred at rt for 2 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (100:0 to 0:100 v/v) as eluent to give 0.81 of OE28 as yellow resin.

    Example 29: Preparation of OE29

    [0456] ##STR00103##

    [0457] OE29 is prepared according to the following scheme:

    ##STR00104## ##STR00105##

    Preparation of IM29-1

    [0458] To 17.93 g of 9-ethylhexylcarbazole and 8.61 g of aluminum chloride in DCM (100 ml) was added 10.96 g of 4-methoxybenzoyl chloride and stirred at rt for 4 h under N.sub.2 flow condition. The reaction mixture was poured into ice-water and extracted with ethyl acetate, then, dried over anhydrous sodium sulfate. The crude was purified via column chromatography with hexane and DCM (100:0 to 50:50 v/v) as eluent to give 6.19 g of IM29-1 as yellow resin.

    Preparation of IM29-2

    [0459] To 6.19 g of IM29-1 and 1.68 g of azelaoyl chloride in chlorobenzene (100 ml), 6.09 g of potassium carbonate was added and stirred at rt for 3 h, then, heated at 100° C. for 4 h. The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane/DCM/acetone (90:10:0 to 0:80:20 v/v/v) as eluent to give 9.90 g of IM29-2 as orange resin.

    Preparation of IM29-3

    [0460] To 3.04 g of IM29-3 was added mixture of DMF (100 ml), tetrahydrofuran (100 ml) and hydrochloric acid (40 ml) at 0° C. Then, 3.02 g of amyl nitrite was added and stirred for 4 h at rt. The organic layer was extracted with TBME and washed with brine, then, dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 80:20 v/v) as eluent to give 0.86 g of IM29-3 as yellow resin.

    Preparation of OE29

    [0461] To 0.86 of IM29-3 and 1.06 g of acetyl chloride in tetrahydrofuran (100 ml) was added 1.34 g of triethylamine at 0° C., then stirred at rt for 2 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane/DCM/acetone (90:10:0 to 0:95:5 v/v/v) as eluent to give 0.30 of OE29 as yellow resin.

    Example 30: Preparation of OE30

    [0462] ##STR00106##

    [0463] OE30 is prepared according to following scheme:

    ##STR00107##

    Preparation of IM30-1

    [0464] To 2.38 g of (9-ethylcarbazol-3-yl)-(4-methoxyphenyl)methanone and 1.18 g of 3-cyclopentylpropionyl chloride in chlorobenzene (30 ml) was added 3.14 g of aluminum chloride and stirred at rt for 16 h under N.sub.2 flow condition, then heated at 100° C. for 1 h. The reaction mixture was poured into ice-water, and added ethyl acetate and hexane. Then, the precipitate was collected by filtration and washed with mixture of hexane and DCM. The resulting solid was dried in vacuo to give 4.26 g of IM30-1 as beige solid.

    Preparation of IM30-2

    [0465] To 4.26 g of IM30-1 and 1.38 g of butyl chloroformate in tetrahydrofuran (50 ml), 1.05 g of triethylamine was added at 0° C. and stirred for 16 h. The organic layer was extracted with TBME and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 1.27 g of IM30-2 as off-white resin.

    Preparation of IM30-3

    [0466] To 1.27 g of IM30-2 and 0.80 g of sodium nitrite were added mixture of DMF (20 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (10 ml) was dropwise and stirred for 20 h. The organic layer was extracted with ethyl acetate, then, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 0.86 g of IM30-3 as orange resin.

    Preparation of OE30

    [0467] To 0.86 of IM30-2 and 0.31 g of acetyl chloride in tetrahydrofuran (50 ml) was added 0.45 g of triethylamine at 0° C., then stirred at room temperature for 16 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 0.50 g of OE30 as yellow resin.

    Example 31: Preparation of OE31

    [0468] ##STR00108##

    [0469] OE31 is prepared according to the following scheme:

    ##STR00109## ##STR00110## ##STR00111##

    Preparation of IM31-1

    [0470] To 10.80 g of carbazole and 8.64 g of aluminum chloride in DCM (100 ml) was added 11.04 g of 4-methoxybenzoyl chloride and stirred at rt for 4 h under N.sub.2 flow condition. The reaction mixture was poured into ice-water and added hexane, then, precipitation was filtered. The resulting solid was dried in vacuo to give 11.43 g of IM31-1 as beige solid.

    Preparation of IM31-2

    [0471] To 6.57 g of IM31-1 and 2.20 g of 1,3-dibromopropane in dimethyl sulfoxide (20 ml) was added 2.65 g of potassium hydroxide (85% purity) at rt for 16 h. The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 90:10 v/v) as eluent to give 2.65 g of IM31-2 as brown resin.

    Preparation of IM31-3

    [0472] To 2.65 of IM31-2 and 1.34 g of 3-cyclopentylpropionyl chloride in chlorobenzene (30 ml) was added 3.89 g of aluminum chloride and stirred at rt for 16 h under N.sub.2 flow condition, then heated at 100° C. for 1 h. The reaction mixture was poured into ice-water, and added ethyl acetate and hexane. Then, the precipitate was collected by filtration and washed with the mixture of hexane and DCM. The resulting solid was dried in vacuo to give 2.01 g of IM31-3 as off-white powder.

    Preparation of IM31-4

    [0473] To 2.01 g of IM31-3 and 0.77 g of butyl chloroformate in tetrahydrofuran (50 ml), 0.97 g of triethylamine was added at 0° C. and stirred for 16 h. The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 95:5 v/v) as eluent to give 1.01 g of IM31-4 as pale brown resin.

    Preparation of IM31-5

    [0474] To 1.01 g of IM31-4 and 0.52 g of sodium nitrite were added mixture of DMF (20 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (4 ml) was dropwise and stirred for 20 h. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 95:5 v/v) as eluent to give 0.46 g of IM31-5 as pale yellow resin.

    Preparation of OE31

    [0475] To 0.46 of IM31-5 and 0.65 g of acetyl chloride in tetrahydrofuran (30 ml) was added 0.83 g of triethylamine at 0° C., then stirred at room temperature for 16 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 98:2 v/v) as eluent to give 0.41 g of OE31 as yellow resin.

    Example 32: Preparation of OE32

    [0476] ##STR00112##

    [0477] OE32 is prepared according to the following scheme:

    ##STR00113##

    Preparation of IM32-1

    [0478] To mixture of 4.42 g of (9-ethylcarbazol-3-yl)-(4-methoxyphenyl)methanone and 2.49 g of 2,5-dimethylphenylacetyl chloride in chlorobenzene (50 ml) was added 6.18 g of aluminum chloride and stirred at rt for 16 h under N.sub.2 flow condition, then heated at 100° C. for 1 h. The reaction mixture was poured into ice-water, and added DCM and hexane. Then, the precipitate was collected by filtration and washed with mixture of hexane and DCM. The resulting solid was dried in vacuo to give 7.23 g of IM32-1 as off-white solid.

    Preparation of IM32-2

    [0479] To 3.99 g of IM32-1 and 1.90 g of sodium nitrite were added mixture of DMF (50 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (10 ml) was dropwise and stirred for 20 h. The organic layer was extracted with ethyl acetate, then, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 97:3 v/v) as eluent to give 1.64 g of IM32-2 as yellow solid.

    Preparation of OE32

    [0480] To 1.64 of IM32-2 and 0.61 g of acetyl chloride in tetrahydrofuran (50 ml) was added 0.74 g of triethylamine at 0° C., then stirred at room temperature for 16 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 1.21 g of OE32 as yellow resin.

    [0481] The product OE32 was obtained mainly in E configuration. Samples of pure E isomer and pure Z isomer were prepared using conventional silica gel chromatography (DCM/Acetone). The Z isomer of OE32 (OE32-Z) can be prepared according to the following scheme:

    ##STR00114##

    Preparation of IM32-2Z

    [0482] To 3.99 g of IM32-1 and 1.90 g of sodium nitrite were added mixture of DMF (50 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (10 ml) was dropwise and stirred for 20 h. The organic layer was extracted with ethyl acetate, then washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude product was purified via column chromatography with DCM and acetone (100:0 to 97:3 v/v) as eluent to give 1.64 g of IM32-2 as yellow solid. The solid was isolated by filtration and washed with heptane, which was (mainly) composed of E-isomer. The filtrate was purified by silica gel chromatography (DCM/Acetone) to give 0.44 g of IM32-2Z (Z isomer).

    Preparation of OE32-Z

    [0483] To 0.44 g of IM32-2 and 0.61 g of acetyl chloride in tetrahydrofuran (13.5 ml) was added 0.20 g of triethylamine at 0° C., then stirred at room temperature for 16 h. Water was added to the reaction mixture and the organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude product was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 0.33 g of OE32-Z as yellow resin.

    Example 34: Preparation of OE34

    [0484] ##STR00115##

    [0485] OE34 is prepared according to the following scheme:

    ##STR00116## ##STR00117##

    Preparation of IM34-1

    [0486] To IM17-2 (7.82 g) and glutaryl chloride (1.30 g) in THF (25 mL) was added triethylamine (1.71 g) in TH (5 mL) dropwise under cooling with a water bath. After stirring for 30 h at room temperature, water and then EtOAc were added to this reaction mixture. The organic layer was washed with K.sub.2CO.sub.3 aq. solution, water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-hexane mixture as eluent. IM34-1 was obtained as pale yellow resin (2.81 g).

    Preparation of IM34-2

    [0487] To IM34-1 (2.12 g) and sodium nitrite (0.32 g) in DMF (6 mL) was added isopropyl alcohol (0.4 mL). To this reaction mixture was added HCl in dioxane solution (4M, 3.0 mL) dropwise at room temperature, and the mixture was stirred for 26.5 h. Water and then EtOAc were added to this reaction mixture, and the organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM34-2 was obtained as yellow resin (1.41 g).

    Preparation of OE34

    [0488] To IM34-2 (0.47 g) and acetyl chloride (0.14 g) in EtOAc (6 mL) was added triethylamine (0.21 g) in EtOAc (2 ml) dropwise at room temperature. After stirring for 16.5 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE34 was obtained as yellow resin (0.35 g).

    Example 35: Preparation of OE35

    [0489] ##STR00118##

    [0490] OE35 is prepared according to the following scheme:

    ##STR00119## ##STR00120##

    Preparation of IM35-1

    [0491] To nitromethane (10 mL) were added AlCl.sub.3 (6.69 g) and then carbazole (8.37 g) in nitromethane (15 ml) under cooling with an ice bath, followed by adding 4-methoxybenzoyl chloride (8.54 g) dropwise. After stirring for 3 h at room temperature, to this reaction mixture were added n-octanoyl chloride (8.04 g) in nitromethane (5 ml) and then AlCl.sub.3 (7.06 g) in portions. The reaction mixture was stirred for 2.5 h and then poured onto ice. The product was extracted with EtOAc, and the organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was washed with CH.sub.2Cl.sub.2. IM35-1 was obtained as dark yellow solid (11.23 g).

    Preparation of IM35-2

    [0492] To IM35-1 (0.86 g) and 4-bromobutyric acid ethyl ester (0.59 g) in DMA (5 mL) was added K.sub.2CO.sub.3 (0.56 g). The reaction mixture was stirred at room temperature for 17.5 h. Water was added to this reaction mixture, and the products were extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM35-2 was obtained as pale yellow resin (0.55 g).

    Preparation of IM35-3

    [0493] IM35-2 (0.54 g) and AlCl.sub.3 (0.61 g) were combined in chlorobenzene (10 mL) and heated at 80° C. for 2 h. The reaction mixture was poured onto ice, and the product was extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the crude product (0.52 g) was used for the next reaction without further purification.

    Preparation of IM35-4

    [0494] To the crude IM35-3 (0.52 g) and sodium nitrite (0.088 g) in DMF (3 mL) was added isopropyl alcohol (0.15 mL). To this reaction mixture was added HCl in dioxane solution (4M, 0.8 mL) dropwise at room temperature, and the mixture was stirred for 15.5 h. Water and then EtOAc were added to this reaction mixture, and the organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM35-4 was obtained as yellow resin (0.38 g).

    Preparation of OE35

    [0495] To IM35-4 (0.33 g) and acetyl chloride (0.19 g) in THF (7 mL) was added triethylamine (0.31 g) in THF (1 mL) dropwise at room temperature. After stirring for 2.5 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE35 was obtained as yellow resin (0.31 g).

    Example 36: Preparation of OE36

    [0496] ##STR00121##

    [0497] OE36 is prepared as the following scheme.

    ##STR00122##

    Preparation of IM36-1

    [0498] To 4.58 g of IM3-1 and 1.80 g of diethyl chlorophosphate in tetrahydrofuran (50 ml), 1.56 g of potassium carbonate and 1 ml of pyridine was added and stirred at 70° C. for 16 h. The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 97:3 v/v) as eluent to give 4.83 g of IM36-1 as yellow resin.

    Preparation of IM36-2

    [0499] To 4.83 g of IM36-1 and 1.09 g of sodium nitrite were added mixture of DMF (20 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (10 ml) was dropwise and stirred for 20 h. The organic layer was extracted with ethyl acetate, then, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 90:10 v/v) as eluent to give 3.50 g of IM36-2 as yellow resin.

    Preparation of OE36

    [0500] To 3.50 of IM36-2 and 0.51 g of acetyl chloride in tetrahydrofuran (100 ml) was added 0.62 g of triethylamine at 0° C., then stirred at rt for 16 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 97:3 v/v) as eluent to give 2.06 of OE36 as yellow resin.

    [0501] The product OE36 was obtained mainly in E configuration. Samples of pure E isomer and pure Z isomer were prepared using conventional silica gel chromatography (DCM/Acetone). The Z isomer of OE36 (OE36-Z) can be prepared according to the following scheme:

    ##STR00123##

    Preparation of IM36-2Z

    [0502] To 4.83 g of IM36-1 and 1.09 g of sodium nitrite were added mixture of DMF (20 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (10 ml) was dropwise and stirred for 20 h. The organic layer was extracted with ethyl acetate, then washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude product was purified via column chromatography with DCM and acetone (100:0 to 90:10 v/v) as eluent to give 0.50 g of IM36-2Z as yellow resin.

    Preparation of OE36-Z

    [0503] To 0.50 g of IM36-2Z and 0.07 g of acetyl chloride in tetrahydrofuran (15 ml) was added 0.09 g of triethylamine at 0° C., then stirred at rt for 16 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude product was purified via column chromatography with hexane and acetone (100:0 to 97:3 v/v) as eluent to give 0.50 g of OE36-Z as yellow resin.

    Example 37: Preparation of OE37

    [0504] ##STR00124##

    [0505] OE37 is prepared according to the following scheme:

    ##STR00125##

    Preparation of IM37-1

    [0506] To 4.76 g of IM3-1 and 1.60 g of 2-thenoyl chloride in tetrahydrofuran (50 ml), 1.61 g of potassium carbonate and 1 ml of pyridine was added and stirred at 70° C. for 4 h. The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and 5.61 g of crude IM37-1 was obtained as off-white solid.

    Preparation of IM37-2

    [0507] To 4.83 g of IM37-1 and 1.95 g of sodium nitrite were added mixture of DMF (50 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (20 ml) was dropwise and stirred for 20 h. The organic layer was extracted with ethyl acetate, then, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 97:3 v/v) as eluent to give 2.04 of IM37-2 as orange resin.

    Preparation of OE37

    [0508] To 2.04 of IM37-2 and 0.34 g of acetyl chloride in tetrahydrofuran (50 ml) was added 0.40 g of triethylamine at 0° C., then stirred at rt for 16 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and acetone (100:0 to 99:1 v/v) as eluent to give 1.94 of OE37 as yellow resin.

    Example 38: Preparation of OE38

    [0509] ##STR00126##

    [0510] OE38 is prepared according to the following scheme:

    ##STR00127##

    Preparation of IM38-1

    [0511] To IM17-3 (13.02 g) in t-butyl methyl ether (80 mL) was added acetic anhydride (4.93 g) in t-butyl methyl ether (10 mL) at room temperature. After stirring for 17 h, the resulting precipitate was collected by filtration and washed with t-butyl methyl ether. IM38-1 was obtained as white solid (10.54 g).

    Preparation of OE38

    [0512] To IM38-1 (0.58 g) and phenyl chloroformate (0.19 g) in THF (5 mL) was added triethylamine (0.14 g) in THF (1 mL) dropwise at room temperature. After stirring for 16 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE38 was obtained as yellow resin (0.31 g).

    Example 39: Preparation of OE39

    [0513] ##STR00128##

    [0514] OE39 is prepared according to the following scheme:

    ##STR00129## ##STR00130##

    Preparation of IM39-1

    [0515] To a solution of Fluorobenzene (10.0 g, 104 mmol) and Aluminum Chloride (13.9 g, 104 mmol) in DCM (400 ml) was added Octanoyl chloride (16.9 g, 104 mmol) at 0° C., and the mixture was stirred for 3 days at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. Silica gel and Potassium carbonate was added to the solution. The inorganic salts were removed by cotton filtration, and washed with DCM. The solvent was removed under reduced pressure to give the product (18.0 g, 78%).

    Preparation of IM39-2

    [0516] To a solution of Carbazole (4.66 g, 27.9 mmol) and IM39-1 (6.20 g, 27.9 mmol) in DMA (250 ml) was added NaH 60% in oil (1.34 g, 33.5 mmol) at 0° C., and the mixture was stirred for overnight at 120° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (5.66 g, 55%).

    Preparation of IM39-3

    [0517] To a solution of IM39-2 (5.66 g, 15.3 mmol) and Aluminum Chloride (4.2 g, 13.6 mmol) in DCM (150 ml) was added 4-Methoxybenzoyl chloride (2.61 g, 15.3 mmol) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added Octanoyl Chloride (2.6 ml, 15.2 mmol) and Aluminum Chloride (2.1 g, 15.8 mmol), and the mixture was stirred for 30 mi. To the reaction mixture was added Aluminum Chloride (2.1 g, 15.8 mmol), and the mixture was stirred for overnight at the reflux temperature. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (6.50 g, 69%).

    Preparation of IM39-4

    [0518] To a solution of IM39-3 (3.03 g, 4.92 mmol) in DMF (25 ml) was added Isopropyl alcohol (1.1 ml, 14 mmol), Sodium nitrite (0.85 g, 12 mmol) and 4 M HCl Dioxane (7.4 ml, 30 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (2.25 g, 68%).

    Preparation of OE39

    [0519] To a solution of IM39-4 (2.25 g, 3.34 mmol) in TBME (100 ml) was added TEA (1.5 ml, 11 mmol) and Acetic anhydride (1.0 ml, 11 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched by water. The mixture was extracted with TBME, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (1.72 g, 64%).

    Example 40: Preparation of OE40

    [0520] ##STR00131##

    [0521] OE40 is prepared according to the following scheme:

    ##STR00132##

    Preparation of IM40-1

    [0522] To a solution of 9-Phenylcarbazole (5.00 g, 20.5 mmol) and Aluminum Chloride (3.01 g, 22.6 mmol) in DCM (200 ml) was added 4-Methoxybenzoyl chloride (3.50 g, 20.5 mmol) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added Aluminum Chloride (3.01 g, 22.6 mmol) and Octanoyl Chloride (3.33 g, 20.5 mmol), and the mixture was stirred for 30 min. To the reaction mixture was added Aluminum Chloride (3.01 g, 22.6 mmol), and the mixture was stirred for overnight at the reflux temperature. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (4.01 g, 40%).

    Preparation of IM40-2

    [0523] To a solution of IM40-1 (2.00 g, 4.09 mmol) in DMF (20 ml) was added Isopropyl alcohol (0.44 ml, 5.7 mmol), Sodium nitrite (0.34 g, 4.93 mmol) and 4 M HCl Dioxane (3.0 ml, 12 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (1.62 g, 76%).

    Preparation of OE40

    [0524] To a solution of IM40-2 (1.62 g, 3.12 mmol) in TBME (30 ml) was added TEA (0.92 ml, 6.6 mmol) and Acetic anhydride (0.62 ml, 6.6 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched by water. The mixture was extracted with TBME, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (4.16 g, 78%).

    Example 41: Preparation of OE41

    [0525] ##STR00133##

    [0526] OE41 is prepared according to the following scheme:

    ##STR00134##

    Preparation of IM41-1

    [0527] To 3.24 g of IM32-1 and 0.97 g of 2-methoxyethyl chloroformate in mixture of tetrahydrofuran (20 ml) and DMF (10 ml), 0.74 g of triethylamine was added at 0° C. and stirred for 16 h. The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and 1.66 g of crude IM41-1 was obtained as orange resin.

    Preparation of IM41-2

    [0528] To 1.66 g of crude IM41-1 and 1.01 g of sodium nitrite were added mixture of DMF (20 ml) and isopropyl alcohol (10 ml) at rt. Then, 4M of hydrochloric acid in dioxane solution (6 ml) was dropwise and stirred for 20 h. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with DCM and acetone (100:0 to 97:3 v/v) as eluent to give 1.31 g of IM41-2 as yellow resin.

    Preparation of OE41

    [0529] To 1.31 of IM41-2 and 0.28 g of acetyl chloride in tetrahydrofuran (30 ml) was added 0.35 g of triethylamine at 0° C., then stirred at room temperature for 16 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and DCM (90:10 to 0:100 v/v) as eluent to give 0.90 g of OE41 as yellow resin.

    Example 42: Preparation of OE42

    [0530] ##STR00135##

    [0531] OE42 is prepared as the following scheme.

    ##STR00136##

    Preparation of IM42-1

    [0532] To a solution of 9-ethylcarbazole (0.98 g, 5 mmol) and Aluminum Chloride (0.73 g, 5.5 mmol) in Chlorobenzene (20 ml) was added 4-Methoxybenzoyl chloride (0.85 g, 5 mmol) at 0° C., and the mixture was stirred for 1 h. To the reaction mixture was added Aluminum Chloride (1.46 g, 11 mmol) and cyclopentylacetyl chloride (0.74 g, 5 mmol), and the mixture was stirred for 1 h. Then, the mixture was stirred for 3 h at 80° C. The reaction mixture was quenched with cold water. The reaction mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product (1.8 g, 86%).

    Preparation of IM42-2

    [0533] To a solution of IM42-1 (0.9 g, 2.0 mmol) in DMF (10 ml) was added conc. HCl (3.6 ml, 6 mmol) and Amyl Nitrite (0.35 g, 6 mmol) at 0° C., and the mixture was stirred for overnight at rt. The reaction mixture was quenched with cold water. The reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and DCM/Hexane was added to the crude product. The precipitated solid was collected by filtration and washed with DCM/Hexane to give the product (0.92 g, 98%).

    Preparation of OE42

    [0534] To a solution of the IM42-2 (0.92 g, 2 mmol) in AcOEt (15 ml) was added TEA (0.7 g, 7 mmol) and Ac.sub.2O (0.6 g, 6 mmol) at rt, and the mixture was stirred for 2 h. The reaction mixture was quenched with water. The mixture was extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product (0.6 g, 60%).

    Example 44: Preparation of OE44

    [0535] ##STR00137##

    [0536] OE44 is prepared according to the following scheme:

    ##STR00138##

    Preparation of IM44-1

    [0537] To IM35-1 (1.28 g) and tetrahydrofurfuryl bromide (1.19 g) in DMA (11 mL) was added K.sub.2CO.sub.3 (0.56 g).

    [0538] The reaction mixture was stirred at room temperature overnight and then heated at 120° C. for 4.5 h. Water was added to this reaction mixture, and the products were extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM44-1 was obtained as white solid (1.27 g).

    Preparation of IM44-2

    [0539] IM44-1 (1.25 g) and AlCl.sub.3 (1.46 g) were combined in chlorobenzene (10 mL) and heated at 80° C. for 2 h. The reaction mixture was poured onto ice, and the product was extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was washed with TBME-hexane mixture to give IM44-2 as white solid (1.11 g).

    Preparation of IM44-3

    [0540] To IM44-2 (1.11 g) and sodium nitrite (0.27 g) in DMF (6.3 mL) was added isopropyl alcohol (0.35 mL). To this reaction mixture was added HCl in dioxane solution (4M, 2.5 mL) dropwise at room temperature, and the mixture was stirred for 27 h. Water and then EtOAc were added to this reaction mixture, and the organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM44-3 was obtained as yellow resin (0.61 g).

    Preparation of OE44

    [0541] To IM44-3 (0.59 g) and acetyl chloride (0.36 g) in THF (9 mL) was added triethylamine (0.59 g) in THF (2 mL) dropwise at room temperature. After stirring for 2 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE44 was obtained as yellow resin (0.48 g).

    Example 45: Preparation of OE45

    [0542] ##STR00139##

    [0543] OE45 is prepared according to the following scheme:

    ##STR00140##

    Preparation of IM45-1

    [0544] To IM35-1 (1.28 g) and 1-bromo-3-methoxypropane (0.96 g) in DMA (10 mL) was added K.sub.2CO.sub.3 (0.89 g). The reaction mixture was heated at 120° C. for 3 h. Water was added to this reaction mixture, and the products were extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM45-1 was obtained as yellow resin (1.03 g).

    Preparation of IM45-2

    [0545] IM45-1 (1.00 g) and AlCl.sub.3 (1.18 g) were combined in chlorobenzene (10 mL) and heated at 80° C. for 2 h. The reaction mixture was poured onto ice, and the product was extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was washed with TBME to give IM45-2 as pale beige solid (0.83 g).

    Preparation of IM45-3

    [0546] To IM45-2 (0.83 g) and sodium nitrite (0.15 g) in DMF (4.0 mL) was added isopropyl alcohol (0.26 mL). To this reaction mixture was added HCl in dioxane solution (4M, 1.3 mL) dropwise at room temperature, and the mixture was stirred for 23 h. Water and then EtOAc were added to this reaction mixture, and the organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM45-3 was obtained as yellow resin (0.64 g).

    Preparation of OE45

    [0547] To IM45-3 (0.63 g) and acetyl chloride (0.39 g) in THF (9 mL) was added triethylamine (0.63 g) in THF (3 mL) dropwise at room temperature. After stirring for 2 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE45 was obtained as yellow resin (0.56 g).

    Example 46: Preparation of OE46

    [0548] ##STR00141##

    [0549] OE46 is prepared according to the following scheme:

    ##STR00142##

    Preparation of OE46

    [0550] To IM38-1 (0.71 g) and terephthaloyl chloride (0.13 g) in THF (5 mL) was added triethylamine (0.15 g) in THF (1 mL) dropwise at room temperature. After stirring for 22.5 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE46 was obtained as yellow resin (0.61 g).

    Example 47: Preparation of OE47

    [0551] ##STR00143##

    [0552] OE47 is prepared according to the following scheme:

    ##STR00144##

    Preparation of OE47

    [0553] To IM38-1 (0.59 g) and ethyl succinyl chloride (0.21 g) in THF (5 mL) was added triethylamine (0.14 g) in THF (1 mL) dropwise at room temperature. After stirring for 26.5 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE47 was obtained as yellow resin (0.53 g).

    Example 48: Preparation of OE48

    [0554] ##STR00145##

    [0555] OE48 is prepared according to the following scheme:

    ##STR00146##

    Preparation of OE48

    [0556] To IM38-1 (0.58 g) and phenylacetyl chloride (0.19 g) in THF (5 mL) was added triethylamine (0.13 g) in THF (1 mL) dropwise at room temperature. After stirring for 26 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE48 was obtained as yellow resin (0.57 g).

    Example 49: Preparation of OE49

    [0557] ##STR00147##

    [0558] OE49 is prepared according to the following scheme:

    ##STR00148##

    Preparation of OE49

    [0559] To IM38-1 (0.58 g) and ethyl chloroglyoxylate (0.17 g) in THF (5 mL) was added triethylamine (0.14 g) in THF (1 mL) dropwise at room temperature. After stirring for 26 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was solidified from TBME-hexane mixture under cooling with a dry ice-acetone bath. The resulting solid was washed with hexane to give OE48 as white solid (0.34 g).

    Example 50: Preparation of OE50

    [0560] ##STR00149##

    [0561] OE50 is prepared according to the following scheme:

    ##STR00150##

    Preparation of OE50

    [0562] To IM38-1 (0.59 g) and allyl chloroformate (0.15 g) in THF (5 mL) was added triethylamine (0.14 g) in THF (1 mL) dropwise at room temperature. After stirring for 16 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE50 was obtained as yellow resin (0.57 g).

    Example 51: Preparation of OE51

    [0563] ##STR00151##

    [0564] OE51 is prepared according to the following scheme.

    ##STR00152##

    Preparation of IM51-1

    [0565] To IM43-1 (4.27 g) and 1-bromo-3-methoxypropane (2.30 g) in DMA (20 mL) was added K.sub.2CO.sub.3 (2.22 g). The reaction mixture was heated at 120° C. for 21 h. Water was added to this reaction mixture, and the products were extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM51-1 was obtained as white solid (2.58 g).

    Preparation of IM51-2

    [0566] IM51-1 (2.58 g) and AlCl.sub.3 (3.05 g) were combined in chlorobenzene (20 mL) and heated at 80° C. for 2 h. The reaction mixture was poured onto ice, and the product was extracted with EtOAc. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM51-2 was obtained as white solid (2.39 g).

    Preparation of IM51-3

    [0567] To IM51-2 (2.38 g) and sodium nitrite (0.41 g) in DMF (9.8 mL) was added isopropyl alcohol (0.75 mL). To this reaction mixture was added HCl in dioxane solution (4M, 4.0 mL) dropwise at room temperature, and the mixture was stirred for 4.5 h. Water and then EtOAc were added to this reaction mixture, and the organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. The collected solid was further washed with TBME-hexane mixture to give IM51-3 as pale yellow solid (1.72 g).

    Preparation of OE51

    [0568] To IM51-3 (0.44 g) in THF (4 mL) were added acetic anhydride (0.20 g) in THF (1 mL) and then triethylamine (0.21 g) in THF (1 mL) dropwise at room temperature. After stirring for 21.5 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE51 was obtained as pale yellow solid (0.42 g).

    Example 52: Preparation of OE52

    [0569] ##STR00153##

    [0570] OE52 is prepared according to the following scheme:

    ##STR00154##

    Preparation of IM52-1

    [0571] To IM42-2 (0.52 g) in THF (5 mL) was added acetic anhydride (0.24 g) in THF (1 mL) at room temperature. After stirring for 21 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM52-1 was obtained as yellow resin (0.48 g).

    Preparation of OE52

    [0572] To IM52-1 (0.47 g) and ethyl chloroformate (0.16 g) in THF (6 mL) was added triethylamine (0.17 g) in THF (1 mL) dropwise at room temperature. After stirring for 20 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE52 was obtained as pale yellow solid (0.46 g).

    [0573] The product OE52 was obtained mainly in E configuration. Samples of pure E isomer and pure Z isomer were prepared using conventional silica gel chromatography (DCM/Acetone). The Z isomer of OE52 (OE52-Z) can be prepared according to the following scheme:

    ##STR00155##

    Preparation of IM52-1Z

    [0574] To IM42-2 (0.52 g), which was (mainly) composed of E-isomer, in THF (5 mL) was added acetic anhydride (0.24 g) in THF (1 mL) at room temperature. After stirring for 21 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM52-1Z was obtained as yellow resin (0.11 g).

    Preparation of OE52-Z

    [0575] To IM52-1Z (0.11 g) and ethyl chloroformate (0.04 g) in THF (1.5 mL) was added triethylamine (0.04 g) in THF (1 mL) dropwise at room temperature. After stirring for 20 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE52-Z (Z isomer) was obtained as pale yellow solid (0.11 g)

    Example 53: Preparation of OE53

    [0576] ##STR00156##

    [0577] OE53 is prepared according to the following scheme:

    ##STR00157##

    Preparation of IM53-1

    [0578] To IM51-3 (1.28 g) in THF (15 mL) was added acetic anhydride (0.78 g) in THF (2 mL) at room temperature. After stirring for 41 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. IM53-1 was obtained as yellow solid (1.13 g).

    Preparation of OE53

    [0579] To IM53-1 (0.33 g) and ethyl chloroformate (0.099 g) in THF (4 mL) was added triethylamine (0.10 g) in THF (1 mL) dropwise at room temperature. After stirring for 16.5 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE53 was obtained as pale yellow resin (0.31 g).

    Example 54: Preparation of OE54

    [0580] ##STR00158##

    [0581] OE54 is prepared according to the following scheme:

    ##STR00159##

    Preparation of OE54

    [0582] To IM53-1 (0.81 g) and azelaoyl chloride (0.17 g) in THF (5 mL) was added triethylamine (0.19 g) in THF (1 mL) dropwise at room temperature. After stirring for 16.5 h, water and then EtOAc were added to this reaction mixture. The organic layer was washed with water and brine, followed by drying over anhydrous MgSO.sub.4. After filtration and concentration, the residue was applied to silica gel column chromatography with CH.sub.2Cl.sub.2-acetone mixture as eluent. OE53 was obtained as yellow resin (0.45 g).

    Example 56: Preparation of OE56

    [0583] ##STR00160##

    [0584] OE56 is the same as IM36-1.

    Compound List and Physical Data Thereof

    [0585]

    TABLE-US-00001 Oxime ester (OE) Structure .sup.1H NMR in CDCl.sub.3 OE1  [00161]embedded image 1.00 (d, 6H), 1.50 (t, 3H), 2.02-2.12 (m, 1H), 2.28 (s, 3H), 2.80 (d, 2H), 4.45 (q, 2H), 7.40 (d, 2H), 7.48-7.58, (m, 4H), 7.68 (t, 1H), 7.96 (d, 2H), 8.08 (d, 1H), 8.25 (d, 2H), 8.34 (d, 1H), 8.70 (s, 1H), 8.94 (s, 1H) OE2  [00162]embedded image 0.98 (d, 3H), 1.48 (t, 3H), 2.28 (s, 3H), 2.35 (s, 3H), 2.80 (d, 2H), 4.45 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.34 (d, 1H), 8.68 (s, 1H), 8.90 (s, 1H) OE3  [00163]embedded image 0.86 (t, 3H), 1.26-1.68 (m, 11H), 2.29 (s, 3H), 2.37 (s, 3H), 2.85 (t, 2H), 4.46 (q, 2H), 7.28 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.31 (dd, 1H), 8.67 (s, 1H), 8.87 (s, 1H) OE4  [00164]embedded image 0.88 (t, 3H), 1.50 (t, 3H), 2.29 (s, 3H), 2.37 (s, 3H), 2.87 (q, 2H), 4.46 (q, 2H), 7.28 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.30 (dd, 1H), 8.66 (s, 1H), 8.87 (s, 1H) OE5  [00165]embedded image 0.90 (t, 3H), 1.36-1.65 (m, 8H), 2.28 (s, 3H), 2.35 (s, 3H), 2.86 (t, 2H), 4.45 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.88 (s, 1H) OE6  [00166]embedded image 1.50 (t, 3H), 2.28 (s, 3H), 2.35 (s, 3H), 2.37 (s, 3H), 4.50 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.88 (s, 1H) OE7  [00167]embedded image 1.00 (t, 3H), 1.48 (t, 3H), 1.60-1.72 (m, 2H), 2.28 (s, 3H), 2.35 (s, 3H), 2.84 (t, 2H), 4.45 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.88 (s, 1H) OE8  [00168]embedded image 0.85 (t, 3H), 1.25-1.68 (m, 13H), 2.29 (s, 3H), 2.37 (s, 3H), 2.85 (t, 2H), 4.46 (q, 2H), 7.28 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.31 (dd, 1H), 8.67 (s, 1H), 8.87 (s, 1H) OE9  [00169]embedded image 0.85 (t, 3H), 0.92 (t, 3H), 1.30-1.50 (m, 10H), 1.50 (t, 3H), 1.55-1.65 (m, 2H), 1.75-1.82 (m, 2H), 2.28 (s, 3H), 2.60 (t, 2H), 2.85 (t, 2H), 4.45 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.86 (s, 1H) OE10 [00170]embedded image 0.98 (t, 3H), 1.02 (t, 3H), 1.45-1.54 (m, 5H), 1.60-1.70 (m, 2H), 1.75-1.82 (m, 2H), 2.28 (s, 3H), 2.60 (t, 2H), 2.85 (t, 2H), 4.50 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.86 (s, 1H) OE11 [00171]embedded image 0.90 (t, 3H), 0.95 (t, 3H), 1.45-1.52 (m, 9H), 1.55-1.62 (m, 2H), 1.75-1.85 (m, 2H), 2.28 (s, 3H), 2.60 (t, 2H), 2.85 (t, 2H), 4.50 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.86 (s, 1H) OE12 [00172]embedded image 0.85 (t, 3H), 1.25-1.30 (m, 4H), 1.35-1.45 (m, 2H), 1.50 (t, 3H), 1.60-1.70 (m, 2H), 2.30 (s, 3H), 2.85 (t, 2H), 4.42 (q, 2H), 7.28 (t, 2H), 7.38-7.52 (m, 6H), 7.54- 7.60 (m, 3H), 7.87 (dd, 1H), 8.30 (dd, 1H), 8.35 (d, 1H), 8.82 (d, 1H) OE13 [00173]embedded image 0.85 (t, 3H), 1.25-1.30 (m, 4H), 1.35-1.45 (m, 2H), 1.50 (t, 3H), 1.65-1.75 (m, 2H), 1.96 (s, 3H), 2.30 (s, 3H), 2.85 (t, 2H), 4.42 (q, 2H), 7.28 (d, 1H), 7.38 (t, 1H), 7.45 (dd, 2H), 7.56 (dd, 2H), 8.00 (d, 1H), 8.28 (d, 1H), 8.64 (s, 1H), 8.84 (s, 1H) OE14 [00174]embedded image 0.92 (t, 3H), 1.35 (d, 6H), 1.35-1.45 (m, 2H), 1.50 (t, 3H), 1.65-1.75 (m, 2H), 2.28 (s, 3H), 2.80-2.90 (m, 3H), 4.50 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.86 (s, 1H) OE15 [00175]embedded image 1.15 (t, 3H), 1.48 (t, 3H), 2.26 (s, 3H), 2.35 (s, 3H), 2.72 (t, 2H), 3.14 (t, 2H), 4.05 (q, 2H), 4.50 (q, 2H), 7.28 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.88 (s, 1H) OE16 [00176]embedded image 0.87 (t, 3H), 0.94 (t, 6H), 1.20-1.50 (m, 10H), 1.56-1.67 (m, 2H), 2.01-2.12 (m, 1H), 2.29 (s, 3H), 2.37 (s, 3H), 2.86 (dd, 2H), 4.25 (d, 2H), 7.27 (d, 2H), 7.48, (d, 2H), 7.92 (d, 2H), 8.05 (dd, 1H), 8.30 (dd, 1H), 8.66 (d, 1H), 8.87 (d, 1H) OE17 (E) [00177]embedded image 0.85 (t, 3H), 0.88 (t, 3H), 0.94 (t, 3H), 1.20-1.45 (m, 12H), 1.60-1.68 (m, 2H), 2.02-2.10 (m, 1H), 2.28 (s, 3H), 2.36 (s, 3H), 2.84 (t, 2H), 4.50 (d, 2H), 7.28 (d, 2H), 7.48, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.86 (s, 1H) OE17 (Z) [00178]embedded image 0.86 (t, 3H), 0.87 (t, 3H), 0.95 (t, 3H), 1.20-1.45 (m, 12H), 1.60-1.70 (m, 2H), 2.02-2.10 (m, 1H), 2.36 (s, 3H), 2.38 (s, 3H), 2.70 (t, 2H), 4.27 (d, 2H), 7.28 (d, 2H), 7.52, (d, 2H), 7.92 (d, 2H), 8.02 (d, 1H), 8.09 (d, 1H), 8.63 (s, 1H), 8.64 (s, 1H) OE18 [00179]embedded image 0.85 (t, 3H), 0.86 (t, 3H), 0.92 (t, 3H), 1.20-1.45 (m, 16H), 1.58-1.65 (m, 2H), 2.02-2.10 (m, 1H), 2.26 (s, 3H), 2.36 (s, 3H), 2.84 (t, 2H), 4.50 (d, 2H), 7.28 (d, 2H), 7.48, (d, 2H), 7.90 (d, 2H), 8.04 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.86 (s, 1H) OE19 [00180]embedded image 0.95 (t, 3H), 1.43-1.61 (m, 10H), 2.29 (s, 3H), 2.86 (t, 2H), 4.38 (q, 2H), 4.46 (q, 2H), 7.36 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.32 (dd, 1H), 8.67 (s, 1H), 8.88 (s, 1H) OE20 [00181]embedded image 0.88 (t, 3H), 1.25-1.60 (m, 15H), 2.29 (s, 3H), 2.37 (t, 3H), 2.84 (t, 2H), 4.37 (q, 2H), 4.45 (q, 2H), 7.37 (d, 2H), 7.50, (dd, 2H), 7.91 (d, 2H), 8.04 (dd, 1H), 8.29 (dd, 1H), 8.66 (s, 1H), 8.87 (s, 1H) OE21 [00182]embedded image 0.85 (t, 3H), 1.25-1.68 (m, 17H), 2.29 (s, 3H), 2.85 (t, 2H), 4.38 (q, 2H), 4.48 (q, 2H), 7.36 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.30 (dd, 1H), 8.66 (s, 1H), 8.88 (s, 1H) OE22 [00183]embedded image 1.00 (t, 3H), 1.02 (t, 3H), 1.48 (t, 3H), 1.60-1.70 (m, 2H), 1.75-1.85 (m, 2H), 2.26 (s, 3H), 3.84 (t, 2H), 4.25 (t, 2H), 4.50 (q, 2H), 7.35 (d, 2H), 7.50 (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.88 (s, 1H) OE23 [00184]embedded image 0.93 (t, 3H), 1.05 (t, 3H), 1.36-1.48 (m, 2H), 1.51 (t, 3H), 1.54-1.66 (m, 2H), 1.76- 1.87 (m, 2H), 2.29 (s, 3H), 2.86 (dd, 2H), 4.27 (t, 2H), 4.46 (q, 2H), 7.37 (d, 2H), 7.51 (d, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.31 (dd, 1H), 8.67 (d, 1H), 8.88 (d, 1H) OE24 [00185]embedded image 0.86 (t, 3H), 1.04 (t, 3H), 1.30-1.40 (m, 4H), 1.50 (t, 3H), 1.56-1.65 (m, 2H), 1.76- 1.85 (m, 2H), 2.26 (s, 3H), 2.84 (t, 2H), 4.25 (t, 2H), 4.50 (q, 2H), 7.35 (d, 2H), 7.50, (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.88 (s, 1H) OE25 [00186]embedded image 0.91 (t, 3H), 1.00 (t, 3H), 1.25-1.81 (m, 11H), 2.29 (s, 3H), 2.86 (t, 2H), 4.31 (t, 2H), 4.46 (q, 2H), 7.37 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.31 (dd, 1H), 8.66 (s, 1H), 8.88 (s, 1H) OE26 [00187]embedded image 0.88 (t, 3H), 1.00 (t, 3H), 1.29-1.81 (m, 13H), 2.29 (s, 3H), 2.85 (t, 2H), 4.32 (t, 2H), 4.46 (q, 2H), 7.37 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.31 (dd, 1H), 8.66 (s, 1H), 8.88 (s, 1H) OE27 [00188]embedded image 0.92 (t, 3H), 1.04 (d, 6H), 1.38-1.65 (m, 9H), 2.05-2.14 (m, 1H), 2.28 (s, 3H), 2.85 (t, 2H), 4.20 (d, 2H), 4.45 (q, 2H), 7.35 (d, 2H), 7.50 (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.30 (d, 1H), 8.65 (s, 1H), 8.88 (s, 1H) OE28 [00189]embedded image 0.86-0.95 (m, 9H), 1.24-1.68 (m, 20H), 2.03-2.10 (m, 1H), 2.29 (s, 3H), 2.85 (t, 2H), 3.42-3.50 (m, 4H), 4.20-4.30 (m, 2H), 7.30 (d, 2H), 7.48 (d, 2H), 7.90 (d, 2H), 8.05 (d, 1H), 8.29 (d, 2H), 8.65 (s, 1H), 8.85 (s, 1H) OE29 [00190]embedded image 0.86 (t, 6H), 0.92 (t, 6H), 1.26-2.09 (m, 24H), 2.26 (s, 6H), 2.36 (s, 6H), 2.84 (t, 4H), 4.22-4.24 (m, 4H), 7.26 (d, 4H), 7.91 (4H), 7.44-7.49 (m, 4H), 8.04 (dd, 2H), 8.26 (dd, 2H), 8.64 (s, 2H), 8.85 (s, 2H) OE30 [00191]embedded image 0.99 (t, 3H), 1.22-1.27 (m, 2H), 1.49-1.79 (m, 12H), 2.10-2.18 (m, 1H), 2.29 (s, 3H), 2.94 (d, 2H), 4.32 t, 2H), 4.46 (q, 2H), 7.36 (d, 2H), 7.51 (d, 2H), 7.92 (d, 2H), 8.05 (dd, 1H), 8.32 (dd, 1H), 8.68 (s, 1H), 8.91 s, 1H) OE31 [00192]embedded image 1.00 (t, 6H), 1.20-1.26 (m, 4H), 1.49-1.80 (m, 14H), 2.10-2.18 (m, 2H), 2.28 (s, 6H), 2.92 (d, 4H), 4.31 (t, 6H), 4.51 (t, 4H), 7.30-7.38 (m, 8H), 7.90 (d, 4H), 7.98 (dd, 2H), 8.26 (dd, 2H), 8.68 (s, 2H), 8.92 (s, 2H) OE32 (E) [00193]embedded image 1.52 (t, 3H), 2.16 (s, 3H), 2.17 (s, 3H), 2.32 (s, 3H), 2.36 (s, 3H), 4.47 (q, 2H), 7.08 (s, 1H), 7.16-7.29 (m, 4H), 7.54 (t, 2H), 7.92 (d, 2H), 8.07 (dd, 1H), 8.42 (dd, 1H), 8.70 (s, 1H), 9.04 (s, 1H) OE32 (Z) [00194]embedded image 1.52 (t, 3H), 1.98 (s, 3H), 2.20 (s, 3H), 2.36 (s, 3H), 2.68 (s, 3H), 4.47 (q, 2H), 7.08 (s, 1H), 7.16-7.29 (m, 4H), 7.54 (t, 2H), 7.88 (d, 2H), 8.10 (dd, 1H), 8.41 (dd, 1H), 8.62 (s, 1H), 8.75 (s, 1H) OE34 [00195]embedded image 0.86-0.90 (m, 12H), 0.93 (t, 6H), 1.20- 1.48 (m, 24H), 1.57-1.68 (m, 4H), 2.00- 2.13 (m, 2H), 2.23-2.36 (m, 2H), 2.30 (s, 6H), 2.80-2.90 (m, 8H), 4.25 (d, 4H), 7.30 (d, 4H), 7.48 (d, 4H), 7.94 (d, 4H), 8.05 (dd, 2H), 8.29 (dd, 2H), 8.66 (d, 2H), 8.87 (d, 2H) OE35 [00196]embedded image 0.86 (t, 3H), 1.22-1.35 (m, 7H), 1.35-1.45 (m, 2H), 1.56-1.68 (m, 2H), 2.19-2.28 (m, 2H), 2.29 (s, 3H), 2.34-2.40 (m, 2H), 2.37 (s, 3H), 2.85 (dd, 2H), 4.16 (q, 2H), 4.49 (t, 2H), 7.28 (d, 2H), 7.54 (d, 1H), 7.55 (d, 1H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.30 (dd, 1H), 8.66 (d, 1H), 8.87 (d, 1H) OE36 (E) [00197]embedded image 0.86 (t, 3H), 1.24-1.69 (m, 17H), 2.30 (s, 3H), 2.85 (t, 2H), 4.25-4.30 (m, 4H), 4.38 (q, 2H), 7.38 (d, 2H), 7.51 (dd, 2H), 7.88 (d, 2H), 8.03 (dd, 1H), 8.30 (dd, 1H), 8.65 (s. 1H), 8.87 (s, 1H) OE36 (Z) [00198]embedded image 0.86 (t, 3H), 1.24-1.69 (m, 17H), 1.88 (s, 3H), 2.69 (t, 2H), 4.25-4.30 (m, 4H), 4.38 (q, 2H), 7.39 (d, 2H), 7.53 (dd, 2H), 7.87 (d, 2H), 8.07 (dd, 1H), 8.30 (dd, 1H), 8.62 (s. 1H), 8.87 (s, 1H) OE37 [00199]embedded image 0.86 (t, 3H), 1.25-1.71 (m, 11H), 2.29 (s, 3H), 2.86 (t, 2H), 4.46 (q, 2H), 7.22 (dd, 1H), 7.41 (d, 2H), 7.51 (dd, 2H), 7.72 (dd, 1H), 7.96 (d, 2H), 8.04 (dd, 1H), 8.08 (dd, 1H), 8.31 (dd, 1H), 8.68 (s, 1H), 8.89 (s, 1H) OE38 [00200]embedded image 0.87 (t, 3H), 0.88 (t, 3H), 0.94 (t, 3H), 1.20-1.48 (m, 12H), 1.57-1.68 (m, 2H), 2.00-2.14 (m, 1H), 2.28 (s, 3H), 2.85 (dd, 2H), 4.26 (d, 2H), 7.28-7.35 (m, 3H), 7.42-7.53 (m, 6H), 7.96 (d, 2H), 8.06 (dd, 1H), 8.30 (dd, 1H), 8.66 (d, 1H), 8.88 (d, 1H) OE39 [00201]embedded image 0.86 (t, 3H), 0.88 (t, 3H), 1.24-1.46 (m, 12H), 1.58-1.68 (m, 4H), 2.28 (s, 3H), 2.90 (s, 3H), 2.36 (s, 3H), 2.84 (t, 2H), 2.86 (t, 2H), 7.28 (d, 2H), 7.52 (dd, 2H), 7.72 (d, 2H), 7.92 (d, 2H), 7.98 (dd, 1H), 8.24 (dd, 1H), 2.41 (d, 2H), 8.70 (d, 1H), 8.92 (d, 1H) OE40 [00202]embedded image 0.86 (t, 3H), 1.24-1.32 (m, 4H), 1.35-1.45 (m, 2H), 1.56-1.66 (m, 2H), 2.28 (s, 3H), 2.36 (s, 3H), 2.84 (t, 2H), 7.26 (d, 2H), 7.42 (dd, 2H), 7.56 (dt, 3H), 7.66 (t, 2H), 7.92 (d, 2H), 7.97 (dd, 1H), 8.22 (dd, 1H), 8.70 (d, 1H), 8.92 (d, 1H) OE41 [00203]embedded image 1.52 (t, 3H), 2.16 (s, 3H), 2.32 (s, 3H), 3.46 (s, 3H), 3.72 (t, 2H), 4.43-4.50 (m, 4H), 7.08-7.23 (m, 3H), 7.37 (d, 2H), 7.51-7.56 (m, 2H), 7.91 (d, 2H), 8.07 (dd, 1H), 8.42 (dd, 1H), 8.69 (s, 1H), 9.04 (s, 1H) OE42 [00204]embedded image 1.45-2.11 (m, 12H), 2.28 (s, 3H), 2.38 (s, 3H), 4.46 (q, 2H), 7.37 (d, 2H), 7.51, (dd, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.31 (dd, 1H), 8.64 (s, 1H), 8.75 (s, 1H) OE44 [00205]embedded image 0.86 (t, 3H), 1.21-1.35 (m, 4H), 1.35-1.45 (m, 2H), 1.56-1.73 (m, 3H), 1.74-1.95 (m, 2H), 1.99-2.11 (m, 1H), 2.29 (s, 3H), 2.37 (s, 3H), 2.85 (t, 2H), 3.68-3.85 (m, 2H), 4.35-4.57 (m, 3H), 7.27 (d, 2H), 7.58 (d, 1H), 7.59 (d, 1H), 7.92 (d, 2H), 8.05 (dd, 1H), 8.29 (dd, 1H), 8.65 (d, 1H), 8.85 (d, 1H) OE45 [00206]embedded image 0.86 (t, 3H), 1.22-1.46 (m, 6H), 1.56-1.69 (m, 2H), 2.11-2.21 (m, 2H), 2.29 (s, 3H), 2.37 (s, 3H), 2.86 (t, 2H), 3.26 (t, 2H), 3.13 (s, 3H), 4.53 (t, 2H), 7.27 (d, 2H), 7.56 (d, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.30 (dd, 1H), 8.66 (d, 1H), 8.86 (d, 1H) OE46 [00207]embedded image 0.88 (t, 6H), 0.89 (t, 6H), 0.95 (t, 6H), 1.21-1.50 (m, 24H), 1.59-1.69 (m, 4H), 2.02-2.15 (m, 2H), 2.30 (s, 6H), 2.86 (dd, 4H), 4.27 (d, 4H), 7.46 (d, 4H), 7.49 (d, 2H), 7.52 (d, 2H), 8.01 (d, 4H), 8.10 (dd, 2H), 8.31 (dd, 2H), 8.42 (s, 4H), 8.70 (d, 2H), 8.90 (d, 2H) OE47 [00208]embedded image 0.83-0.91 (m, 6H), 0.94 (t, 3H), 1.20-1.48 (m, 12H), 1.30 (t, 3H), 1.58-1.68 (m, 2H), 2.00-2.12 (m, 1H), 2.29 (s, 3H), 2.78 (t, 2H), 2.85 (dd, 2H), 2.95 (t, 2H), 4.21 (q, 2H), 4.25 (d, 2H), 7.28 (d, 2H), 7.48 (d, 2H), 7.92 (d, 2H), 8.04 (dd, 1H), 8.29 (dd, 1H), 8.66 (d, 1H), 8.87 (d, 1H) OE48 [00209]embedded image 0.86 (t, 3H), 0.88 (t, 3H), 0.93 (t, 3H), 1.20-1.48 (m, 12H), 1.57-1.67 (m, 2H), 2.00-2.12 (m, 1H), 2.26 (s, 3H), 2.84 (dd, 2H), 3.93 (s, 2H), 4.24 (d, 2H), 7.25 (d, 2H), 7.31-7.45 (m, 5H), 7.48 (d, 2H), 7.90 (d, 2H), 8.04 (dd, 1H), 8.29 (dd, 1H), 8.64 (d, 1H), 8.86 (d, 1H) OE49 [00210]embedded image 0.87 (t, 3H), 0.88 (t, 3H), 0.94 (t, 3H), 1.20-1.70 (m, 14H), 1.47 (t, 3H), 2.00- 2.12 (m, 1H), 2.29 (s, 3H), 2.85 (dd, 2H), 4.26 (d, 2H), 4.49 (q, 2H), 7.39 (d, 2H), 7.48 (d, 1H), 7.50 (d, 1H), 7.96 (d, 2H), 8.06 (dd, 1H), 8.30 (dd, 1H), 8.66 (d, 1H), 8.89 (d, 1H) OE50 [00211]embedded image 0.83-0.91 (m, 6H), 0.94 (t, 3H), 1.20-1.50 (m, 12H), 1.58-1.69 (m, 2H), 2.00-2.12 (m, 1H), 2.30 (s, 3H), 2.85 (dd, 2H), 4.25 (d, 2H), 4.79 (d, 2H), 5.38 (d, 1H), 5.47 (d, 1H), 6.04 (ddt, 1H), 7.37 (d, 2H), 7.48 (d, 1H), 7.49 (d, 1H), 7.93 (d, 2H), 8.05 (dd, 1H), 8.30 (dd, 1H), 8.66 (d, 1H), 8.88 (d, 1H) OE51 [00212]embedded image 1.18-1.31 (m, 2H), 1.44-1.72 (m, 4H), 1.73-1.84 (m, 2H), 2.11-2.22 (m, 3H), 2.29 (s, 3H), 2.37 (s, 3H), 2.93 (d, 2H), 3.27 (t, 2H), 3.32 (s, 3H), 4.53 (t, 2H), 7.27 (d, 2H), 7.56 (d, 2H), 7.92 (d, 2H), 8.05 (dd, 1H), 8.32 (dd, 1H), 8.68 (d, 1H), 8.90 (d, 1H) OE52 (E) [00213]embedded image 1.43 (t, 3H), 1.51 (t, 3H), 1.58-1.82 (m, 6H), 1.93-2.10 (m, 2H), 2.29 (s, 3H), 3.48-3.61 (m, 1H), 4.38 (q, 2H), 4.42- 4.52 (m, 2H), 7.34-7.40 (m, 2H), 7.48- 7.56 (m, 2H), 7.92 (d, 2H), 8.06 (dd, 1H), 8.24 (dd, 1H), 8.63-8.68 (m, 1H), 8.78 (d, 1H) OE52 (Z) [00214]embedded image 1.43 (t, 3H), 1.53 (t, 3H), 1.58-1.82 (m, 6H), 1.88 (s, 3H), 1.93-2.10 (m, 2H), 3.07-3.18 (m, 1H), 4.38 (q, 2H), 4.42- 4.52 (m, 2H), 7.34-7.40 (m, 2H), 7.48- 7.56 (m, 2H), 7.91 (d, 2H), 8.02 (dd, 1H), 8.09 (dd, 1H), 8.63-8.68 (m, 2H) OE53 [00215]embedded image 1.18-1.32 (m, 2H), 1.43 (t, 3H), 1.47-1.56 (m, 2H), 1.58-1.72 (m, 2H), 1.72-1.85 (m, 2H), 2.10-2.23 (m, 3H), 2.29 (s, 3H), 2.93 (d, 2H), 3.27 (t, 2H), 3.32 (s, 3H), 4.38 (q, 2H), 4.53 (t, 2H), 7.37 (d, 2H), 7.56 (d, 2H), 7.92 (d, 2H), 8.05 (dd, 1H), 8.32 (dd, 1H), 8.67 (d, 1H), 8.90 (d, 1H) OE54 [00216]embedded image 1.18-1.33 (m, 4H), 1.42-1.72 (m, 14H), 1.72-1.90 (m, 8H), 2.10-2.23 (m, 6H), 2.29 (s, 6H), 2.65 (t, 4H), 2.93 (d, 4H), 3.26 (t, 4H), 3.32 (s, 6H), 4.52 (t, 4H), 7.27 (d, 4H), 7.55 (d, 4H), 7.91 (d, 4H), 8.04 (dd, 2H), 8.31 (dd, 2H), 8.67 (d, 2H), 8.90 (d, 2H) OE56 [00217]embedded image 0.82-0.90 (m, 6H), 0.93 (t, 3H), 1.20-1.50 (m, 12H), 1.58-1.68 (m, 2H), 2.00-2.13 (m, 1H), 2.30 (s, 3H), 2.85 (dd, 2H), 4.24 (d, 2H), 5.68 (s, 1H), 6.95 (d, 2H), 7.47 (d, 1H), 7.48 (d, 1H), 7.83 (d, 2H), 8.02 (dd, 1H), 8.28 (dd, 1H), 8.59 (d, 1H), 8.85 (d, 1H)

    APPLICATION EXAMPLES

    Sensitivity Test: A

    Preparation of Color Filter Resist (Blue)

    [0586] Blue pigment dispersion is prepared by mixing the following components and dispersing them by using a Paint conditioner (SKANDEX).

    Blue Dispersion

    [0587]

    TABLE-US-00002  5.6 parts by weight blue pigment (PB15:6, Blue E provided by Toyo Ink)  0.6 parts by weight violet pigment (PV23, Cromophtal Violet GA provided by BASF)  2.6 parts by weight dispersant (EFKA6745 provided by BASF)  0.4 parts by weight synergist (Solsperse S5000 provided by Lubrizol) 19.6 parts by weight solvent (PGMEA)

    [0588] Color filter resist (blue) are prepared by further adding the following components to the above dispersion prepared.

    TABLE-US-00003  6.0 parts by weight alkaline developable binder, 37.8% solution (Ripoxy SPC-2000, provided by Shoko Highpolymer) 41.9 parts by weight solvent (PGMEA)  5.0 parts by weight multifunctional acrylate (DPHA, provided by Sigma-Aldrich)  0.7 parts by weight Photoinitiator

    [0589] All operations are carried out under yellow light. The compositions are applied to a glass plate using a spincoater. The solvent is removed by heating at 80° C. for 10 minutes in a convection oven. Exposure is carried out using a 250 W super high pressure mercury lamp (USHIO, USH-250BY) at a distance of 15 cm. A total exposure dose measured by an optical power meter (ORC UV Light Measure Model UV-M02 with UV-35 detector) on the glass filter is 50 mJ/cm.sup.2. After exposure, the exposed film is baked at 230° C. for 30 minutes in a forced convention oven. The film is measured transmittance from 350 nm to 780 nm after drying, exposure and baking using UV-VIS spectrometer (Shimazu, UV-2550). Y value at 0.094 of y is calculated from transmittance of the film. Y value means brightness of the film after baking 230° C. for 30 minutes. Larger Y value indicates higher brightness. The results are listed in Table 1.

    TABLE-US-00004 TABLE 1 Brightness Example No. PI Y Example A1  OE1  10.47 Example A2  OE2  10.47 Example A3  OE3  10.48 Example A4  OE4  10.49 Example A5  OE5  10.50 Example A6  OE6  10.51 Example A7  OE7  10.50 Example A8  OE8  10.50 Example A9  OE9  10.48 Example A10 OE10 10.48 Example A11 OE11 10.48 Example A12 OE12 10.46 Example A13 OE13 10.46 Example A14 OE14 10.53 Example A15 OE15 10.48 Example A17 OE17 10.5* Example A18 OE18 10.47 Example A19 OE19 10.48 Example A20 OE20 10.5 Example A21 OE21 10.49 Example A22 OE22 10.51 Example A23 OE23 10.5 Example A24 OE24 10.53 Example A25 OE25 10.52 Example A26 OE26 10.53 Example A27 OE27 10.48 Example A28 OE28 10.44 Example A29 OE29 10.49 Example A30 OE30 10.49 Example A31 OE31 10.51 Example A32 OE32 10.51* Example A34 OE34 10.47 Example A35 OE35 10.52 Example A36 OE36 10.44* Example A37 OE37 10.46 Example A38 OE38 10.49 Example A39 OE39 10.49 Example A40 OE40 10.53 Example A41 OE41 10.45 Example A42 OE42 10.49 Example A44 OE44 10.50 Example A45 OE45 10.50 Example A46 OE46 10.50 Example A47 OE47 10.50 Example A48 OE48 10.51 Example A49 OE49 10.51 Example A50 OE50 10.49 Example A51 OE51 10.51 Example A52 OE52 10.50* Example A53 OE53 10.53 Example A54 OE54 10.54 Example A56 OE56 10.51 Comparative example CE1 10.37 Comparative example CE2 10.03 Comparative example CE3 10.43 Comparative example CE4 10.43 Comparative example CE5 10.40 *The obtained brightness value Y did not depend on the use of E or Z isomers or mixtures thereof.

    [0590] The following photoinitiators were used in the comparative examples:

    ##STR00218##