Patent ID: 6296785
Filing Date: 2001-10-02
Classification: C07D,G02B

Abstract:
A naphthopyran compound of indeno[2,1-f]naphtho[1,2-b]pyran structure, represented by the following graphic formula I: ##STR24##wherein,(a) in the 7 position, a group R.sub.5 selected from the group consisting of:(i) the group, --OR.sub.8 ', wherein R.sub.8 ' is phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 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, or R.sub.8 ' is the group, --CH(R.sub.9)Q, wherein R.sub.9 is hydrogen or C.sub.1 -C.sub.3 alkyl; and(ii) a group selected from:(1) --N(R.sub.15)R.sub.16 wherein R.sub.15 and R.sub.16 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, phenyl, naphthyl, the heteroaromatic groups, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl and fluorenyl, C.sub.1 -C.sub.8 alkylaryl, C.sub.3 -C.sub.20 cycloalkyl, C.sub.4 -C.sub.20 bicycloalkyl, C.sub.5 -C.sub.20 tricycloalkyl and C.sub.1 -C.sub.20 alkoxyalkyl, wherein said aryl group is phenyl or naphthyl;(2) a nitrogen containing ring represented by the following graphic formula: ##STR25##wherein Y is selected from the group consisting of --CH.sub.2 --, --CH(R.sub.17)--, --C(R.sub.17)(R.sub.17)--, --CH(aryl)--, --C(aryl).sub.2 --, and --C(R.sub.17)(aryl)--, and X is selected from the group consisting of --Y--, --O--, --S--, --(O)--, --S(O.sub.2)--, --NH--, --NR.sub.17 -- and --N-aryl, wherein R.sub.17 is C.sub.1 -C.sub.6 alkyl, said aryl substituent is phenyl or naphthyl, m is the integer 1, 2 or 3, and p is the integer 0, 1, 2, or 3 and when p is O, X is Y; and(3) a group represented by the following graphic formulae: ##STR26##wherein R.sub.19, R.sub.20 and R.sub.21 are each hydrogen, C.sub.1 -C.sub.5 alkyl, phenyl or naphthyl, or the groups R.sub.19 and R.sub.20 together form a ring of 5 to 8 carbon atoms and R.sub.18 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -.sub.6 alkoxy, fluoro or chloro;(b) in the 6 position, a group R.sub.6, said group being the same as R.sub.5, defined hereinbefore; or(c) R.sub.5 and R.sub.6 together form the following graphic formula: ##STR27##wherein J and K are each oxygen or the group --NR.sub.15 --;(d) optionally, in the 8 position, a group R.sub.4, said group being the same as R.sub.5 defined hereinbefore; and(e) in the 3 position, weak to moderate electron donor substituents, and optional substituents at the 5-, 8-, 9-, 10-, 11-, 12- or 13-positions provided that said naphthopyran demonstrates a rating of at least 80 in the Relative .DELTA.OD at Saturation Test.