Patent NZ-336837-A (NZ)
Title: Photochromic heterocyclic fused indenonaphthopyrans and photochromic articles thereof
Inventor: KUMAR ANIL
IPC: C07D495/06
Filed: 1997-09-03
Abstract: An indenonaphthopyran compound represented by formula I or II (shown): wherein, A is an unsubstituted, mono-substituted or disubstituted heterocyclic ring selected from the group consisting of benzothieno, benzofurano and indolo, the 2,3 or 3,2 positions of said heterocyclic ring being fused to the g, h, i, n, o or p side of said indenonaphthopyran, said heterocyclic ring substituents being C1-C6 alkyl, C5-C7 cycloalkyl, C1-C6 alkoxy, chloroor fluoro; R1 and R2 together form an oxo group, a spiro heterocyclic group having 2 oxygen atoms and from 3 to 6 carbon atoms including the spirocarbon atom, or R1 and R2 are each hydrogen, hydroxy, C1-C6 alkyl, C3-C7 cycloalkyl, allyl, phenyl, mono-substituted phenyl, benzyl, mono-substituted benzyl, chloro, fluoro or the group, - C(O)W, wherein each W is hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C1-C6)alkylamino or di(C1-C6)alkylamino, or R1 and R2 are each the group, -OR5, wherein each R5 is C1-C6 alkyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, allyl, the group -CH(R6)X, wherein each R6 is hydrogen or C1-C3 alkyl, each X is -CN, -CF3, or -COOR7, and each R7 is hydrogen or C1-C3 alkyl, or each R5 is the group, -C(O)Y, wherein each Y is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, the unsubstituted, mono- or di-substituted aryl groups, phenyl and naphthyl, phenoxy, mono- or di- (C1-C6)alkyl substituted phenoxy, mono- or di- (C1-C6)alkoxy substituted phenoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, phenylamino, mono- or di- (C1-C6) alkyl substituted phenylamino or mono- or di-(C1-C6)alkoxy substituted phenylamino, each of said phenyl, benzyl and aryl group substituents being C1-C6 alkyl or C1-C6 alkoxy; R3 and R4 are each C1-C6 alkyl, C1-C6 alkoxy, chloro or fluoro, and m and n are each the integers 0, 1 or 2; and B and B' are each selected from the group consisting of: (i) the unsubstituted, mono-, di- and tri- substituted aryl groups, phenyl and naphthyl; (ii) the unsubstituted, mono- and di- substituted aromatic heterocyclic groups pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazolyl and fluorenyl, each of said aryl and aromatic heterocyclic substituents in (i) and (ii) being selected from the group consisting of hydroxy, aryl, mono(C1-C6)alkoxyaryl, di(C1-C6)alkoxyaryl, mono(C1-C6)alkylaryl, di(C1-C6)alkylaryl, bromoaryl, chloroaryl, fluoroaryl, C3-C7 cycloalkylaryl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C3-C7 cycloalkyloxy(C1-C6) alkyl, C3-C7 cycloalkyloxy(C1-C6)alkoxy, aryl (C1-C6) alkyl, aryl (C1-C6) alkoxy, aryloxy, aryloxy(C1-C6)alkyl, aryloxy(C1-C6)alkoxy, mono- and di- (C1-C6)alkylaryl(C1-C6)alkyl, mono- and di- (C1-C6)alkoxyaryl(C1-C6)alkyl, mono- and di-(C1-C6)alkylaryl(C1-C6)alkoxy, mono- and di-(C1-C6)alkoxyaryl(C1-C6)alkoxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, diarylamino, N-(C1-C6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrryl, C1-C6 alkyl, C1-C6 bromoalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4) alkyl, acryloxy, methacryloxy, bromo, chloro and fluoro; (iii) the groups represented by formula III or IV: wherein E is carbon or oxygen and D is oxygen or substituted nitrogen, provided that when D is substituted nitrogen, E is carbon, said nitrogen substituents being selected from the group consisting of hydrogen, C1-C6 alkyl and C2-C6 acyl; each R8 is C1-C6 alkyl, C1-C6 alkoxy, hydroxy, bromo, chloro or fluoro; R9 and R10 are each hydrogen or C1-C6 alkyl; and p is the integer 0, 1 or 2; (iv) C1-C6 alkyl, C1-C6 bromoalkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy(C1-C4)alkyl, C3-C6 cycloalkyl, mono(C1-C6) alkoxy(C3-C6)cycloalkyl, mono(C1-C6)alkyl(C3-C6)-cycloalkyl, bromo(C3-C6)cycloalkyl, chloro (C3-C6) cycloalkyl and fluoro(C3-C6)cyclo-alkyl; and (v) the group represented by formula V: wherein X is hydrogen or C1-C4 alkyl and Z is selected from the unsubstituted, mono-, and di- substituted members of the group consisting of naphthyl, phenyl, furanyl and thienyl, each of said group substituents being C1-C4 alkyl, C1-C4 alkoxy, bromo, fluoro or chloro; or (vi) B and B' taken together form fluoren-9-ylidene, mono- or di-substituted fluoren-9-ylidene or a member selected from the group consisting of saturated C3-C12 spiro-monocyclic hydrocarbon rings, saturated C7-C12 spiro-bicyclic hydrocarbon rings, and saturated C7-C12 spiro-tricyclic hydrocarbon rings, each of said fluoren-9-ylidene substituents being selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy, bromo, fluoro and chloro. Also disclosed is a photochromic article comprising a polymeric organic host material and a photochromic amount of compound I or II.