Microwave assisted straightforward synthetic method for benzimidazole linked quinoxalinones on soluble polymer support

Abstract

The simple and efficient method was developed for the synthesis of benzimidazole linked quinoxalinones on soluble polymer support using microwave conditions. The acid catalyzed condensation of 4-fluoro-3-nitrobenzoic acid with polymer immobilized o-phenylenediamine, ipso-fluoro nucleophilic substitution with various primary amines and cyclization with acetyl chloride are the key steps involved in implemented linear synthesis. In key cyclization step, the regioselective N-acylation at secondary amine with chloroacetyl chloride followed by spontaneous intramolecular ring closure through ortho-amine functionality generate the quinoxaline skeleton under microwave irradiation. The removal of polymer support and exposure of quinoxalines for auto-oxidation finally produce the benzimidazole linked quinoxalinone derivatives with high purity and yields. (C) 2011 Elsevier Ltd. All rights reserved.