Parallel synthesis of novel benzimidazoles on a soluble polymer support

Ling Ju Chang, Manohar V. Kulkarni, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Liquid phase combinatorial synthesis using a soluble polyethylene glycol (PEG) polymer support and commercially available 3-nitro-4-fluoro benzoic acid is carried out in order to create a molecular library of trisubstituted benzimidazoles. The PEG-ester conjugate of 3-nitro-4-fluoro benzoic acid is subjected to ipso-fluoro displacement by various primary amines. The nitro group is reduced under neutral conditions using excess zinc and ammonium chloride, producing the polymer-boundo-phenylene diamines. Reaction of the diamines with different aldehydes results in cyclisation to benzimidazoles. The polymer support is cleaved releasing the desired products in high yields and purity. All reactions are performed at room temperature.

Original languageEnglish
Pages (from-to)288-294
Number of pages7
JournalCentral European Journal of Chemistry
Volume3
Issue number2
DOIs
StatePublished - 1 Apr 2005

Keywords

  • Benzimidazoles
  • Liquid phase synthesis
  • Molecular diversity
  • Polymer support

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