The Chemistry of 5-Oxodihydroisoxazoles. IV. Reactions of Some N-Arylisoxazol-5-ones With Nucleophiles

Abstract

The reactions of ethyl 2-aryl-5-oxo-2,5-dihydroisoxazole-4-carbolate (aryl = phenyl, isoquinolin-1-yl, 2-phenylquinazolin-4-yl and 5-nitropyridin-2-yl) with azide and primary, secondary and tertiary amines, and a number of other nucleophiles are described, and the product formation is rationalized in terms of predominant initial attack by the nucleophile at C3, or abstraction of H 3, of the isoxazole ring.