Photochromic heterocyclic fused indenonaphthopyrans

An indenonaphthopyran compound represented by the following graphic formulae:

• ##STR11## wherein, (a) A is an unsubstituted, mono-substituted or di-substituted 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 C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, chloro or fluoro;
• (b) R.sub.1 and R.sub.2 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 R.sub.1 and R.sub.2 are each hydrogen, hydroxy, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allyl, phenyl, mono-substituted phenyl, benzyl, mono-substituted benzyl, chloro, fluoro or the group, --C(O)W, wherein each W is hydroxy, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C.sub.1 -C.sub.6)alkylamino or di(C.sub.1 -C.sub.6)alkylamino, or R.sub.1 and R.sub.2 are each the group, --OR.sub.5, wherein each R.sub.5 is C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, C.sub.3 -C.sub.7 cycloalkyl, mono(C.sub.1 -C.sub.4)alkyl substituted C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, allyl, the group, --CH(R.sub.6)X' wherein each R.sub.6 is hydrogen or C.sub.1 -C.sub.3 alkyl, each X' is --CN, --CF3, or --COOR.sub.7, and each R.sub.7 is hydrogen or C.sub.1 -C.sub.3 alkyl, or each R.sub.5 is the group, --C(O)Y, wherein each Y is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, an unsubstituted, mono- or di-substituted aryl group selected from phenyl and naphthyl, phenoxy, mono- or di-(C.sub.1 -C.sub.6)alkyl substituted phenoxy, mono- or di-(C.sub.1 -C.sub.6)alkoxy substituted phenoxy, amino, mono(C.sub.1 -C.sub.6)alkylamino, di(C.sub.1 -C.sub.6)alkylamino, phenylamino, mono- or di-(C.sub.1 -C.sub.6)alkyl substituted phenylamino or mono- or di-(C.sub.1 -C.sub.6)alkoxy substituted phenylamino, each of said phenyl, benzyl and aryl group substituents being C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy;
• (c) R.sub.3 and R.sub.4 are each C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, chloro or fluoro, and m and n are each the integers 0, 1 or 2;
• and
• (d) B and B' are each selected from the group consisting of:
• (i) an unsubstituted, mono-, di- and tri-substituted aryl group selected from phenyl and naphthyl;
• (ii) an unsubstituted, mono- and di-substituted aromatic heterocyclic group selected from 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 (d) (i) and (ii) being selected from the group consisting of hydroxy, aryl, mono(C.sub.1 -C.sub.6)alkoxyaryl, di(C.sub.1 -C.sub.6)alkoxyaryl, mono(C.sub.1 -C.sub.6)alkylaryl, di(C.sub.1 -C.sub.6)alkylaryl, bromoaryl, chloroaryl, fluoroaryl, C.sub.3 -C.sub.7 cycloalkylaryl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyloxy, C.sub.3 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.6)alkyl, C.sub.3 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.6)alkoxy, aryl(C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.6)alkoxy, aryloxy, aryloxy(C.sub.1 -C.sub.6)alkyl, aryloxy(C.sub.1 -C.sub.6)alkoxy, mono- and di-(C.sub.1 -C.sub.6)alkylaryl(C.sub.1 -C.sub.6)alkyl, mono- and di-(C.sub.1 -C.sub.6)alkoxyaryl(C.sub.1 -C.sub.6)alkyl, mono- and di-(C.sub.1 -C.sub.6)alkylaryl(C.sub.1 -C.sub.6)alkoxy, mono- and di-(C.sub.1 -C.sub.6)alkoxyaryl(C.sub.1 -C.sub.6)alkoxy, amino, mono(C.sub.1 -C.sub.6)alkylamino, di(C.sub.1 -C.sub.6)alkylamino, diarylamino, N-(C.sub.1 -C.sub.6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrryl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 bromoalkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.6 alkoxy, mono(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.4)alkyl, acryloxy, methacryloxy, bromo, chloro and fluoro;
• (iii) a group represented by one of the following graphic formulae:
• ##STR12## 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, C.sub.1 -C.sub.6 alkyl and C.sub.2 -C.sub.6 acyl;
• each R.sub.8 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxy, bromo, chloro or fluoro;
• R.sub.9 and R.sub.10 are each hydrogen or C.sub.1 -C.sub.6 alkyl;
• and p is the integer 0, 1 or 2;
• (iv) C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 bromoalkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.4)alkyl, C.sub.3 -C.sub.6 cycloalkyl, mono(C.sub.1 -C.sub.6)alkoxy(C.sub.3 -C.sub.6)cycloalkyl, mono(C.sub.1 -C.sub.6)alkyl(C.sub.3 -C.sub.6)-cycloalkyl, bromo(C.sub.3 -C.sub.6)cycloalkyl, chloro(C.sub.3 -C.sub.6)cycloalkyl and fluoro(C.sub.3 -C.sub.6)cyclo-alkyl;
• and
• (v) a group represented by the following graphic formula:
• ##STR13## wherein X is hydrogen or C.sub.1 -C.sub.4 alkyl and Z is selected from an unsubstituted, mono-, and di-substituted members of the group consisting of naphthyl, phenyl, furanyl and thienyl, each of said group substituents being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 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 a saturated C.sub.3 -C.sub.12 spiro-monocyclic hydrocarbon ring, a saturated C.sub.7 -C.sub.12 spiro-bicyclic hydrocarbon ring and a saturated C.sub.7 -C.sub.12 spiro-tricyclic hydrocarbon ring, each of said fluoren-9-ylidene substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, bromo, fluoro and chloro.