In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of aryl-cycloheptene scaffolds. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising an aryl-cycloheptene structure. The disclosed methods utilize abundant starting materials and simple reaction sequences that can be used to modularly and scalably assemble common such cores. In various aspects, the present disclosure pertains to compounds prepared using the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

The disclosure provides processes for preparing 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indanacetonitrile and for preparing sulindac, relating to the field of medicine. The former comprises mixing 6-fluoro-2-methyl-1-indanone, cyanoacetic acid, a first organic solvent and an acetic acid-based catalyst to proceed with a first condensation reaction to give a first condensation reaction solution, which contains 5-fluoro-2-methyl-3-indanacetonitrile; and mixing the first condensation reaction solution, per se, with a base, a second organic solvent and 4-(methylthio)benzaldehyde to proceed with a second condensation reaction to give 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indanacetonitrile. The process is a one-pot process without separation of 5-fluoro-2-methyl-3-indanacetonitrile from the solvent, shortening the synthetic route, simplifying the preparation process and improving the 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indanacetonitrile yield.

The disclosure provides processes for preparing 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indanacetonitrile and for preparing sulindac, relating to the field of medicine. The former comprises mixing 6-fluoro-2-methyl-1-indanone, cyanoacetic acid, a first organic solvent and an acetic acid-based catalyst to proceed with a first condensation reaction to give a first condensation reaction solution, which contains 5-fluoro-2-methyl-3-indanacetonitrile; and mixing the first condensation reaction solution, per se, with a base, a second organic solvent and 4-(methylthio)benzaldehyde to proceed with a second condensation reaction to give 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indanacetonitrile. The process is a one-pot process without separation of 5-fluoro-2-methyl-3-indanacetonitrile from the solvent, shortening the synthetic route, simplifying the preparation process and improving the 5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indanacetonitrile yield.

Disclosed are an n-type semiconductor including compound represented by Chemical Formula 1 or Chemical Formula 2, an image sensor, and an electronic device.

##STR00001##

In Chemical Formula 1 and Chemical Formula 2, each substituent is as defined in the detailed description.

Disclosed are an n-type semiconductor including compound represented by Chemical Formula 1 or Chemical Formula 2, an image sensor, and an electronic device.

##STR00001##

In Chemical Formula 1 and Chemical Formula 2, each substituent is as defined in the detailed description.

Process for the preparation of a compound of Formula (I):

##STR00001## the process comprising the reaction of a compound of Formula (II) with malononitrile in the presence of a base and a palladium catalyst,

##STR00002## wherein X, Y and Z, independently of each other, represent fluoro, chloro or C.sub.1-4alkyl; and L is a leaving group; with the proviso that 1 or 2 of X and Y are, independently of each other, fluoro or chloro.

Process for the preparation of a compound of Formula (I):

##STR00001## the process comprising the reaction of a compound of Formula (II) with malononitrile in the presence of a base and a palladium catalyst,

##STR00002## wherein X, Y and Z, independently of each other, represent fluoro, chloro or C.sub.1-4alkyl; and L is a leaving group; with the proviso that 1 or 2 of X and Y are, independently of each other, fluoro or chloro.

Process for the preparation of a compound of Formula (I), the process comprising the reaction of a compound of Formula (II) with malononitrile in the presence of a base and a palladium catalyst, Formula (II) wherein X, Y and Z, independently of each other, represent fluoro, chloro or C.sub.1-4alkyl; and L is a leaving group; with the proviso that 1 or 2 of X and Y are, independently of each other, fluoro or chloro. ##STR00001##

Process for the preparation of a compound of Formula (I), the process comprising the reaction of a compound of Formula (II) with malononitrile in the presence of a base and a palladium catalyst, Formula (II) wherein X, Y and Z, independently of each other, represent fluoro, chloro or C.sub.1-4alkyl; and L is a leaving group; with the proviso that 1 or 2 of X and Y are, independently of each other, fluoro or chloro. ##STR00001##

Provided is a compound of Chemical Formula 1:

##STR00001##

where R.sub.1 and R.sub.2 are each independently hydrogen, a substituted or unsubstituted C.sub.1-60 alkyl, a substituted or unsubstituted C.sub.1-60 alkoxy, a substituted or unsubstituted C.sub.1-60 haloalkyl, a substituted or unsubstituted C.sub.1-60 haloalkoxy, halogen, cyano, tri(C.sub.1-60 alkyl)silyl, a substituted or unsubstituted C.sub.6-60 aryl, or a substituted or unsubstituted C.sub.2-60 heteroaryl containing at least one of O, N, Si and S,

R.sub.3 and R.sub.4 are each independently hydrogen, deuterium, a substituted or unsubstituted C.sub.1-60 alkyl, a substituted or unsubstituted C.sub.1-60 alkoxy, a substituted or unsubstituted C.sub.1-60 haloalkyl, a substituted or unsubstituted C.sub.1-60 haloalkoxy, halogen, cyano, tri(C.sub.1-60 alkyl)silyl, or a substituted or unsubstituted C.sub.2-60 heteroaryl containing at least one of O, N, Si and S, and

Ar is C.sub.6-60 aryl, or C.sub.2-60 heteroaryl containing at least one of O, N, Si and S, wherein the C.sub.6-60 aryl, or C.sub.2-60 heteroaryl is substituted with 1 to 5 substituents each selected from the group consisting of a substituted or unsubstituted C.sub.1-60 alkyl, a substituted or unsubstituted C.sub.1-60 alkoxy, a substituted or unsubstituted C.sub.1-60 haloalkyl, a substituted or unsubstituted C.sub.1-60 haloalkoxy, halogen, cyano, and tri(C.sub.1-60 alkyl)silyl,

and an organic light emitting device including the same.