COUMARINO-3,4-OXAZOLES

摘要

1464164 Coumarino-3,4-oxazoles CIBAGEIGY AG 28 Oct 1974 [1 Nov 1973] 46550/74 Heading C2C Novel coumarino-3,4-oxazoles of the formula wherein R 1 , R 2 and R3 are independently hydrogen or a non-chromophoric substituent (defined) or R 1 and R 2 are in the ortho-position relative to one another and together represent a non-chromophoric divalent radical, and A represents an optionally non-chromophorically substituted radical of the formula wherein Y represents an optionally non-chromophorically substituted benzoxazol-2-yl, naphthoxazol - 2 - yl, phenanthreno - 91,101 : 4,5- oxazol - 2 - yl (=phenanthroxazolyl - 2), benzotriazol - 2 - yl, naphthotriazol - 2 - yl or phenanthrotriazolyl - 2 radical, Z is as defined under Y or represents an optionally non- chromophorically substituted phenyl, 2-triazolyl, 5 - phenyl - oxdiazol - 2 - yl, pyrazol - 1 - yl or 4,6 - diphenyl - 1,3,5 - triazin - 2 - yl radical, B represents a radical of the formula or -CH=CH- or a 1,4-phenylene, 4,41-diphenylene, 1,4-naphthylene, 2,6-naphthylene, 2,5 - furylene or 2,5 - thienylene radical, or a dibenzofurane, dibenzothiophene-dioxide or 9,10 - dihydrophenanthrylene - 2,7 radical bonded in the 3,7-position to the oxazole radical, m represents the numbers 0, 1 or 2, n and n1 independently represent the number 0 or 1 and p represents the number 1 or 2, such that the sum of n+n1 must be 1 or 2, are prepared by condensing a 3-amino-4-hydroxy-coumarin of the formula with either (i) a carboxylic acid of the formula Q-A wherein Q is -COCl, -COBr, -COOH, -COO alkyl or -CN, at a temperature of from 120‹ to 350‹ C., optionally in the presence of a catalyst, in an inert solvent, or (ii) an aldehyde derivative of the formula A-CHO at a temperature of from 20‹ to 200‹ C. to give an azomethine of the formula and oxidizing the latter to the coumarin oxazole. The novel compounds are useful for the optical brightening of polymeric materials.