Oximes as intermediates or final products in reactions of nitroheteroarenes with nucleophiles in the presence of sodium methoxide-methanol system

✍ Scribed by J. Suwińaski; K. Świerczek; P. Wagner; M. Kubicki; T. Borowiak; J. Stowikowska

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 79 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400318

✦ Synopsis

Abstract

It has been shown that reactions of 4‐nitroimidazoles and some other nitroaromatic systems with phenyl‐acetonitrile in the presence of sodium methoxide in methanol lead to the reduction of the nitro to nitroso group and to the nucleophilic displacement of hydrogen atom at the ring by the respective carbanion followed by tautomerization of the nitroso compound to an oxime. Similar reactions of 4‐nitroimidazoles with such nucleophiles as anions generated from 4‐amino‐1,2,4‐triazole occur with the ring transformation of imidazole into 1,2,4‐oxadiazole derivatives sometimes undergoing further processes in the reaction medium. Structures of some products have been confirmed by X‐ray diffraction analysis.