Patent ID: 6683709
Filing Date: 2004-01-27
Classification: C07D,G02B

Abstract:
A photochromic pyran compound corresponding to formula (I) or formula Ia: whereinR1, R2, R3 and R4 are each independently selected from the group &agr; consisting of subgroups A, Aâ€², and Aâ€³, in which subgroup A consists of hydrogen, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C7) cycloalkyl which may include one or more heteroatoms, aryl, heteroaryl, benzyl, hydroxy, bromine, chlorine, and fluorine; subgroup Aâ€² consists of R1 and R2 or R3 and R4 respectively forming an â€”Oâ€”(CH2)nâ€”Oâ€” group bound to the aromatic ring, wherein n=1 or 2; and subgroup Aâ€³ consists of strongly electron withdrawing groups selected from the group consisting of â€”F3, â€”NO2, â€”CN, and â€”SO2R5, wherein R5 is selected from subgroup A, an strongly electron donating groups selected from the group consisting of thio(C1-C6) alkyl, thiophenyl, thiobenzyl, thiomorpholinyl, morpholinyl, piperidinyl, an azacycloheptanyl, piperazinyl, pyrrolidinyl, pyrazolidinyl, and unsubstituted, monosubstituted, or disubstituted amino, wherein the amine substituents are selected from the group consisting of (C1-C6) alkyl, (C3-C7) cycloalkyl, phenyl, and benzyl, with the proviso that of R1 and R2, and of R3 and R4, respectively, only one member of each pair is a strongly electron withdrawing group or a strongly electron donating group selected from subgroup Aâ€³, G including the central spiro carbon atom represents a saturated or unsaturated ring with 5 to 8 carbon atoms of which at most one may be replaced with a hetero moiety selected from the group consisting of O, S, and NR5, where R5 has the meaning given above wherein at least one aromatic or heteroaromatic ring system selected from the group E is annellated to the ring G, wherein group E consists of benzene, naphthalene, phenanthrene, pyridine, quinoline, furan, thiophene, pyrrole, benzofuran, benzothiophene, indole, and carbazole, and wherein the ring system optionally may have one or more substituents from the group &agr; defined above; B and Bâ€² are independently selected from one of the groups a), b), c) and d) wherein group a) consists of monosubstituted, disubstituted, and trisubstituted aryl selected from the group consisting of phenyl and naphthyl; group b) consists of unsubstituted, monosubstituted and disubstituted heteroaryl selected from the group consisting of pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothieno-2-yl, benzothieno-3-yl or julolidinyl; wherein the substituents of the aryl or heteroaryl in a) and b) are selected from the group consisting of hydroxy, amino, mono(C1-C6) alkylamino, di(C1-C6) alkylamino, mono- and diphenylamino wherein said mono- or diphenylamino is unsubstituted, monosubstituted, or disubstituted on the phenyl ring, piperidinyl, morpholinyl, carbazolyl, unsubstituted, monosubstituted, and disubstituted pyrryl, (C1-C6) alkyl, (C1-C6) alkoxy, bromine, chlorine, and fluorine, wherein the substituents of the phenyl or pyrryl are selected from the group consisting of (C1-C6) alkyl, (C1-C6) alkoxy, bromine, chlorine, and fluorine; group c) consists of structural units having the formulas (V) or (W): â€ƒwherein Y and Z are independently selected from the group consisting of O, S, CH, CH1 or NR9, wherein R9 is selected from the group D consisting of (C1-C6) alkyl, (C1-C6) acyl, phenyl and hydrogen; R6 and R7 independently represent hydrogen or (C1-C6) alkyl; R8 is a substituent selected from the subgroup A defined above, and n is 0, 1, 2 or 3; with the proviso that if Y in formula (V) is NR9, Z is carbon, and in group d) B and Bâ€² together form an unsubstituted, monosubstituted or disubstituted fluorene-9-ylidene radical or a saturated hydrocarbon radical, which is C3-C12 spiro-monocyclic, C7-C12 spiro-bicyclic or spiro-tricyclic, wherein the fluorene substituents are selected from the subgroup A.