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Synthesis of 1,2-bisubstituted benzimidazole: 1,3-Shift mechanism catalyzed by acid or base

✍ Scribed by Ya-Mu Xia; Jia You; Feng-Ke Yang

Publisher: Journal of Heterocyclic Chemistry
Year: 2010
Tongue: English
Weight: 181 KB
Volume: 48
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.531

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✦ Synopsis

Abstract

Benzimidazole ring system is a useful nucleus in medicinal chemistry and is found in many biologically active compounds. An efficient approach for the synthesis of 1,2‐bisubstituted benzimidazoles is presented in this article, and the mechanism of the condensation from 2‐[(2‐aminophenylimino)phenylmethyl]‐4‐bromophenol, using piperdine or acetic acid as catalyst, is studied. 1,3‐Shift of negative hydrogen ion is the key step for this rearrangement reaction, and the influences of catalyst, temperature, substrate, and solvent are also investigated. J. Heterocyclic Chem., 2011.

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