Synthesis and reactions of potassium cyanoacetohydroxamate

Abstract

The reaction of ethyl cyanoacetate with hydroxylamine gave potassium cyanoacetohydroxamate (I), which cyclised under basic conditions to yield the isoxazolone (IIIa). Reactions of (I) with hydroxylamine and acetylacetone gave α-(hydroxyamidino)acetohydroxamic acid (II) and the cyanopyridone (IV), respectively. The reaction with benzoyl chloride yielded three products [the O-benzoyl derivative (V), the isoxazolone (IIIb), and NO-dibenzoylhydroxylamine] in amounts depending on the reaction conditions.