Regioselective piperidine-catalyzed tandem imination-isocyanate annulation to fused tricyclic triazines

Indrajeet J. Barve, Chih Hau Chen, Chih Hsien Kao, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A novel tandem imination-isocyanate-mediated annulation was explored. Ionic liquid-immobilized 2-aminobenzimidazoles react sequentially with aldehydes and isocyanates to give highly functionalized benzimidazole-embedded triazines. The second-stage transformation revealed that the formation of triazinone functionality is entirely regioselective to allow rapid assembly of biologically interesting tricyclic skeletons. In conjunction with the application of microwave irradiation and IL support, this method provides an efficient route to access substituted benzoimidazotriazines.

Original languageEnglish
Pages (from-to)244-249
Number of pages6
JournalACS Combinatorial Science
Volume16
Issue number5
DOIs
StatePublished - 12 May 2014

Keywords

  • benzoimidazotriazine
  • imination
  • ionic liquid
  • isocyanate-mediated annulation
  • microwave
  • tandem reaction

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