Reductive Cleavage of 1,2-Oxazines Promoted by Zinc and Ammonium Chloride; Mild One Pot Preparation of γ-Hydroxy Ketones

Abstract

A facile method for a mild single pot reductive cleavage of 1,2-oxazines to γ-hydroxy ketones was developed using zinc and aqueous ammonium chloride as the reagent in methanol. The reaction involves the reduction of N-O bond of the oxazine and the hydrolysis of the resulting 1,4-iminoalcohol.