Allenes. Part 42. Nucleophilic addition of hydroxylamine to allenic and acetylenic nitriles; synthesis of 3-alkyl-5-amino, 5-amino-3-phenyl-, and 3-amino-5-phenyl-isoxazoles

Abstract

Hydroxylamine adds to allenic nitriles to give 3-alkyl-5-aminoisoxazoles in excellent yield. Hydroxyacetylenic nitriles similarly give 5-amino-3-(1-hydroxyalkyl)isoxazoles. Phenylpropynenitrile under varying conditions of temperature and solvent yields mainly 5-amino-3-phenylisoxazole with varying amounts of 3-amino-5-phenylisoxazole as a by-product.