The Chemistry of N-Hydroxyamidoximes, N-Aminoamidoximes, and Hydrazidines

Abstract

N-Hydroxyamidoximes, N-aminoamidoximes, and hydrazidines belong to a class of compounds with the general formula RC═NX(NHY) where X = OH or NH2, Y = OH or NH2, and R is a linear side chain, carbocycle residue, or heterocycle residue. Their structures are similar to those of amidoximes and amidrazones, but they possess very different synthetic utility and pharmacological properties. There are several reviews published on the synthetic and biological applications of amidrazones and amidoximes. (1-8) However, a comprehensive review on the preparative methods, synthetic utility, and biological applications is missing for this class of compounds thus far. We now attempt to readdress the situation by providing a detailed compilation on the chemistry of N-hydroxyamidoximes, N-aminoamidoximes, and hydrazidines in terms of the structure, preparative methods, reactivity, and biological applications.