Ionic liquid-supported synthesis of dihydroquinazolines and tetrahydroquinazolines under microwave irradiation

Hai Yuan Hsu, Chih Chun Tseng, Banrali Matii, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

An efficient microwave-assisted and water-soluble ionic liquid (IL)-supported synthesis of medicinally important dihydro- and tetrahydroquinazolines has been developed. The protocol involves the S N 2 substitution reaction of IL-bound 4-bromomethyl-3-nitrobenzoic acid with various primary amines to provide IL-bound 4-((alkylamino) methyl)-3-nitrobenzoate under microwave irradiation. Further elaboration followed by sequential cyclization with various isothiocyanates and aldehydes furnished IL-bound target compounds. Cleavage of the IL support by methanolysis gave dihydro- and tetrahydroquinazolines with high purity and excellent yields. The new protocol has the advantages of shorter reaction time, easyworkup process, excellent yields, reduced environmental impact, wide substrate scope, and convenient procedure.

Original languageEnglish
Pages (from-to)241-249
Number of pages9
JournalMolecular Diversity
Volume16
Issue number2
DOIs
StatePublished - 1 May 2012

Keywords

  • Green chemistry
  • Ionic liquid support
  • Microwave-assisted synthesis
  • Tetrahydroquinazolines

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