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

Cheng Ting Chou, Gorakh S. Yellol, Wong Jin Chang, Mei Lian Sun*, Chung-Ming Sun

*Corresponding author for this work

Research output: Contribution to journalArticle

13 Scopus citations

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.

Original languageEnglish
Pages (from-to)2110-2117
Number of pages8
JournalTetrahedron
Volume67
Issue number11
DOIs
StatePublished - 18 Mar 2011

Keywords

  • Benzimidazole
  • Combinatorial parallel synthesis
  • Microwave synthesis
  • Polyethylene glycol
  • Polymer supported synthesis
  • Quinoxalinones

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