Regiospecific synthesis of 1-(5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole-3-methylene)-5-phenyl-1H-1,2,3-triazoles

Abstract

A convenient method to obtain a series of 1-(5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole-3-methylene)-5-phenyl-1H-1,2,3-triazoles by a regiospecific cycloaddition reaction of phenyl acetylenes [Ph-C≡C-R, where R = C(O)CCl 3 , C(O)CHCl 2 , C(OH) 2 CF 3 , CCl 3 and 3-methylisoxazolo-5-carbonyl] with 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole-3-methylene azide is reported, in moderate to good yields (67-80%). From the reaction of a 4-trichloroacetyltriazole derivative with methanol or methylamine it was possible to obtain the corresponding ester and amide derivatives, respectively, by substitution of the trichloromethyl group.