Enantiospecific Synthesis of Imidazoquinazolin-2-ones via Base-Catalyzed Tandem Cyclization

Sunil Kumar, Pei Heng Ho, Indrajeet J. Barve, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A facile protocol for the enantiospecific synthesis of novel (S)-3-substituted imidazo[2, l-b]quinazoline-2-ones via tandem reaction of substituted (S)-3-amino-4-aminomethylbenzoates and cyanogen bromide under basic conditions is explored. This tandem process involves addition reaction of substituted (S)-3-amino-4-aminomethylbenzoates to CNBr to yield 2-imino tetrahydroquinazoline carboxylate intermediates followed by in situ intramolecular aminolysis to afford the triheterocyclic imidazo[2, l-b]quinazoline-2-ones in good yields and high enantiomeric purity.

Original languageEnglish
Pages (from-to)8917-8921
Number of pages5
JournalChemistrySelect
Volume2
Issue number28
DOIs
StatePublished - 1 Jan 2017

Keywords

  • Enantiospecific synthesis
  • imidazoquinazolines
  • intramolecular aminolysis
  • quinazolines
  • tandem protocol

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