Photochromic oxazine compounds and methods for their manufacture

A compound comprising the formula:

• 7
• wherein X is nitrogen or carbon;
• R1 and R2 are each independently hydrogen, hydroxy, nitro, cyano, allyl, a linear or branched (C1-C20)alkyl, (C3-C20)cycloalkyl, (C1-C20)alkoxy, (C1-C20)alkylacetylenyl, phenylacetylenyl, (C1-C20)alkenyl, phenylvinyl, a halogen, a halo(C1-C20)alkyl, halo(C3-C20)cycloalkyl, halo(C1-C20)alkoxy, substituted with at least one halogen atom wherein the halogen is fluoro, chloro, bromo, or iodo, unsubstituted aryl, ary;
• substituted with (C1-C6)alkyl or (C1-C6)alkoxy, or aryloxy, unsubstituted heteroaryl, heteroaryl substituted with (C1-C6)alkyl or (C1-C6)alkoxy, arylalkyl or substituted heteroarylalkyl, heteroarylakyl substituted with (C1-C6)alkyl or (C1-C6)alkoxy, substituted or unsubstituted nitrogen-containing heterocyclic ring, —N(R1)R2 or CON(R1)R2 wherein R1 and R2 are each independently hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, substituted phenyl, phenyl substituted with (C1-C6)alkyl or (C1-C6)alkoxy, or a —OCOR or —COOR or —COR group wherein R is hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, or substituted or unsubstituted aryl or heteroaryl;
• n is an integer from 0 to 4;
• and
• A and A′ are each independently:
• (a) a linear or branched (C1-C12)alkyl, (C3-C12)cycloalkyl, aryl(C1-C6)alkyl, heteroaryl(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C12)alkoxy, halo(C1-C12)alkyl, (C1-C12)haloalkoxy, or (C1-C12)alkylthio;
• (b) unsubstituted or mono- di- or tri-substituted aryl groups;
• (c) unsubstituted or mono-, or di-substituted heteroaromatic groups;
• (d) a group of either of the formulae:
• 8
• wherein B is hydrogen, (C1-C12)alkyl, unsubstituted or mono- or di-substituted aryl;
• (e) unsubstituted or mono-substituted pyrazolyl, pyridyl, imidazolyl, pyrazolinyl, imidazolinyl, or acridinyl, wherein the substituents are each independently (C1-C6)alkyl, (C1-C6)alkoxy, fluoro, chloro, phenyl;
• or
• (f) a group represented by either of the formulae:
• 9
• wherein C and D are each independently carbon, oxygen, (C1-C12)alkyl nitrogen, or (C1-C12)acyl nitrogen and R3 and R4 are each independently hydrogen or (C1-C12)alkyl.