On the Reaction of Chloroglyoximes with Aryl Isocyanates

✍ Scribed by Prof. Dr. S. Witek; Dr. T. Czekański; chem. E.; M. Sc. A. Kaczmarek

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 351 KB
• Volume: 332
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19903320523

✦ Synopsis

Abstract

Reaction of chloroglyoxime 1 with aryl isocyanates yielded monocarbamates 3, and chlorooxime functional group was unchanged. The 1,3‐cycloaddition of nitrile N‐oxides generated from 3 to methyl methacrylate gave isoxazole derivatives 5. Compounds 5 were also obtained by carbamoylation of 3‐formyl‐4‐hydro‐5‐methyl‐5‐methoxycarbonylisoxazole oxime 6.

The selectivity of chloroglyoxime carbamoylation and the poor reactivity of chlorooxime group is general. Examples, involving another oximes and their halogeno derivatives are given.