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Condensation products of 1-aryl-4-carboxy- 2- pyrrolidinones with o-diaminoarenes, o-aminophenol, and their structural studies

✍ Scribed by Marius Mickevicius; Zigmuntas Jonas Beresnevicius; Vytautas Mickevicius; Gema Mikulskiene

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 110 KB
Volume: 17
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20171

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✦ Synopsis

Abstract

A series of 2‐substituted benzimidazoles, benzoxazoles were synthesized by the condensation reactions of 1‐aryl‐4‐carboxy‐2‐pyrrolidinones and aromatic ortho‐diamines or ortho‐aminophenol. Alkylation of benzimidazoles with iodoalkanes led to 1‐aryl‐4‐(1‐alkyl‐1H‐benzimidazol‐2‐yl)‐2‐pyrrolidin‐ ones or 1,3‐dialkylbenzimidazolium iodides. N‐Subs‐ tituted γ‐amino acids were prepared by the hydrolysis of 1‐aryl‐4‐(1H‐benzimidazol‐2‐yl)‐2‐pyrrolidinones in sodium hydroxide solution, followed by treatment with acetic acid. The structure of the synthesized pro‐ ducts was investigated using IR and ^1^H, ^13^C NMR spectra, MM2 molecular mechanics, and AM1 semi‐ empirical quantum mechanical methods. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:47–56, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20171

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