Patent ID: 6153126
Filing Date: 2000-11-28
Classification: C07D

Abstract:
A naphthopyran compound represented by the following graphic formula: ##STR12## wherein, (a) R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allyl, phenyl, mono- or di-substituted phenyl, benzyl, mono-substituted benzyl, naphthyl, mono- or di-substituted naphthyl, C.sub.4 -C.sub.12 bicycloalkyl, linear or branched C.sub.3 -C.sub.12 alkenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzopyridyl and indolyl, each of said phenyl, benzyl, naphthyl and heteroaromatic group substituents being C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, morpholino, di(C.sub.1 -C.sub.6)alkylamino, chloro or fluoro;(b) each R.sub.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, chloro, fluoro, phenyl, mono- and di-substituted phenyl, benzyl or mono-substituted benzyl, C.sub.3 -C.sub.7 cycloalkyl, aryloxy, di(C.sub.1 -C.sub.6)alkylamino, morpholino, thiomorpholino, piperidino, pyridyl, tetrahydroquinolino, isoquinolino, aziridino, diarylamino, N-(C.sub.1 -C.sub.6)alkyl piperizino and N-aryl piperizino, wherein the aryl groups are phenyl or naphthyl, each of said phenyl and benzyl substituents being C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, fluoro and chloro, and n is the integer 0, 1 or 2;(c) 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 heteroaromatic groups pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzopyridyl, indoloyl and fluorenyl, each of said aryl and heteroaromatic substituents in parts (i) and (ii) being selected from the group consisting of hydroxy, phenyl, naphthyl, 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, 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, piperazino, N-(C.sub.1 -C.sub.6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrryl, C.sub.1 -C.sub.6 alkyl, 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) the groups represented by the following graphic formulae: ##STR13## wherein A may be carbon or oxygen and D may be oxygen or substituted nitrogen, provided that when D is substituted nitrogen, A 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.7 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C6 alkoxy, hydroxy, chloro or fluoro; R.sub.8 and R.sub.9 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 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, chloro(C.sub.3 -C.sub.6)cycloalkyl, fluoro(C.sub.3 -C.sub.6)cycloalkyl and C.sub.4 -C.sub.12 bicycloalkyl; and(v) the group represented by the following graphic formula: ##STR14## wherein W may be hydrogen or C.sub.1 -C.sub.4 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 in this part (v) being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluoro or chloro; or(vi) B and B' taken together form fluoren-9-ylidene, mono-, or di-substituted fluoren-9-ylidene or form a member selected from the group consisting of saturated C.sub.3 -C.sub.12 spiro-monocyclic hydrocarbon rings, saturated C.sub.7 -C.sub.12 spirobicylic hydrocarbon rings, and saturated C.sub.7 -C.sub.12 spiro-tricyclic hydrocarbon rings, 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, fluoro and chloro.