Base-catalyzed synthesis of bicyclic 4-aminopyrimidines from the reaction of dinitriles with mononitriles

Serghei Chercheja, Juliet K. Simpson, Hon Wai Lam

Research output: Contribution to journalArticlepeer-review

Abstract

A convenient method for the synthesis of bicyclic 4-aminopyrimidines is described, involving the reaction of dinitriles with mononitriles in the presence of catalytic potassium tert-butoxide. These reactions proceed via the Thorpe-Ziegler cyclization of the dinitrile to form an intermediate beta-cyanoenamine, which then undergoes annulation with the mononitrile in situ. (C) 2011 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3839-3845
Number of pages7
JournalTetrahedron
Volume67
Issue number21
DOIs
Publication statusPublished - 27 May 2011

Keywords

  • 4-Aminopyrimidine
  • Dinitrile
  • Nitrile
  • Cyclization
  • Base catalysis
  • RECEPTOR ANTAGONISTS
  • NITRILES
  • CONDENSATION

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