[Indole]naphthopyrans, preparation, compositions and (co)polymer matrices containing them, synthesis intermediates

Compounds of formula (I):

• in which:
• R1 and R2, identical or different, independently represent:
• hydrogen,
• a linear or branched alkyl group having 1 to 12 carbon atoms,
• a cycloalkyl group having 3 to 12 carbon atoms,
• an aryl or heteroaryl group having 6 to 24 carbon atoms or 4 to 24 carbon atoms respectively in its basic structure and at least one heteroatom selected from sulfur, oxygen and nitrogen;
• said basic structure optionally being substituted with at least one substituent selected from:
• a halogen,
• a linear or branched alkyl group having 1 to 12 carbon atoms,
• a linear or branched alkoxy group having 1 to 12 carbon atoms,
• a linear or branched haloalkyl or haloalkoxy group corresponding respectively to the (C1-C12)alkyl and (C1-C12)alkoxy groups above substituted with at least one halogen atom,
• a linear or branched alkenyl group having 2 to 12 carbon atoms,
• an NH2 group,
• an NHR group, R representing a linear or branched alkyl group having 1 to 6 carbon atoms,
• a
• R′ and R″, identical or different, representing independently a linear or branched alkyl group having 1 to 6 carbon atoms or representing, together with the nitrogen atom to which they are bound, a 5- to 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen optionally being substituted with an R′″ group, wherein the R′″ group is a linear or branched alkyl group having 1 to 6 carbon atoms,
• an epoxy group of formula:
• an aralkyl or heteroaralkyl group, the linear or branched alkyl group having 1 to 4 carbon atoms and the aryl and heteroaryl groups having the definitions given above, or
• said two substituents R1 and R2 together form an adamantyl, a norbornyl, a fluorenylidene, a di(C1-C6)alkylanthracenylidene or a spiro(C5-C6)cycloalkylanthracenylidene group;
• said group optionally being substituted with at least one of the substituents listed above for R1, R2:
• aryl or heteroaryl group;
• R3 represents:
• hydrogen,
• a linear or branched alkyl group having 1 to 12 carbon atoms,
• a cycloalkyl group having 3 to 12 carbon atoms,
• an linear or branched alkoxy group, having 1 to 12 carbon atoms,
• a haloalkyl, a halocycloalkyl or a haloalkoxy group corresponding respectively to the alkyl, cycloalkyl, or alkoxy groups above, substituted with at least one halogen atom,
• an aryl or heteroaryl group having the same definition as that given above for R1, R2,
• an aralkyl or heteroaralkyl group, the linear or branched alkyl group having 1 to 4 carbon atoms and the aryl and heteroaryl groups having the same definitions as those given above for R1, R2,
• an —OCOR6 or —COOR6 group, R6 representing a straight or branched alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms or a phenyl group optionally substituted with at least one of the substituents listed above for the R1, R2 values:
• aryl or heteroaryl;
• R4 represents:
• hydrogen,
• a halogen,
• a linear or branched alkyl group having 1 to 12 carbon atoms,
• a cycloalkyl group having 3 to 12 carbon atoms,
• an linear or branched alkoxy group having 1 to 12 carbon atoms,
• a haloalkyl, a halocycloalkyl or a haloalkoxy group corresponding respectively to the alkyl, cycloalkyl, or alkoxy groups above, substituted with at least one halogen atom,
• an aryl or heteroaryl group having the same definition as that given above for R1, R2,
• an aralkyl or heteroaralkyl group, the linear or branched alkyl group having 1 to 4 carbon atoms and the aryl and heteroaryl groups having the same definitions as those given above for R1, R2,
• an amine or amide group:
• —NH2, —NHR, —CONH2, —CONHR,
• R, R′, R″ having their respective definitions given above for the amine substituents of the R1, R2 values:
• aryl or heteroaryl,
• an —OCOR6 or —COOR6 group, R6 representing a straight or branched alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms or a phenyl group optionally substituted with at least one of the substituents listed above for the R1, R2 values:
• aryl or heteroaryl;
• m and n are, independently, integers of 0 to 4;
• R5 represents:
• hydrogen,
• a linear or branched alkyl group having 1 to 12 carbon atoms,
• a cycloalkyl group having 3 to 12 carbon atoms,
• a linear or branched alkenyl group having 2 to 12 carbon atoms,
• a phenyl or benzyl group, optionally substituted with at least one of the substituents listed above for the R1, R2 values:
• aryl or heteroaryl,
• a —COR7, —COOR7 or —CONHR7 group, R7 representing a straight or branched alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms or a linear or branched alkenyl group having 2 to 12 carbon atoms or a phenyl or benzyl group optionally substituted with at least one of the substituents listed above for the R1, R2 values:
• aryl or heteroaryl,
• a methacryloyl group or an acryloyl group,
• an epoxy group of formula: