Synthesis of 2-Substituted-3-oxo-3-[(aryloxycarbonyl)amino]propanoic Acids, Ethyl 3-{[(1E)-ethoxy(aryloxy)methylene]amino}-2-substituted-3-oxopropanoate, (1Z, 2Z) [Chloro(aryloxy)methylene]hydrazine and Structurally Related Compounds from the Reactions

Abstract

Treatment of the reaction mixture of alkyl or arylmalonyl chlorides and aryl cyanates with water give 2-substituted-3-oxo-3-[(aryloxycarbonyl)amino]propanoic acid (1); while with absolute ethanol ethyl 3-{[(1E)-ethoxy(aryloxy)methylene]amino}-2-substituted-3-oxopropanoate (3) is produced. Aryl 3-chloro-2-substituted-3-oxoprop-anoylcarbamate (2) was obtained from the reaction of alkyl or aryl malonyl chlorides with aryl carbamate. Compound 1 was also obtained from the reaction of compound 2 with water. A mechanism is suggested for the formation compounds 1 and 3. The (1Z, 2Z) [chloro(aryloxy)methylene]hydrazine (5) is isolated from the reaction of alkyl or aryl malonyl chlorie (1 mol) with aryl cyanate (2 mol). Product 5 is also prepared from an equimolar reaction of acetyl or benzoyl chloride with aryl cyanates.