A general and efficient five-step one-pot procedure leading to nitrogen-bridgehead heterocycles containing an imidazole ring

Org Lett. 2007 Jun 7;9(12):2253-6. doi: 10.1021/ol070263z. Epub 2007 May 15.

Abstract

A very simple annulation reaction was designed, allowing an imidazole moiety to be fused onto a range of pyridine-based derivatives. The methodology consists of an activation step via the formation of a pyridinium salt to increase the electrophilicity of the pyridine ring, followed by a cascade reaction triggered by a nucleophilic attack of the iminium moiety. Depending on the pyridinium salt, it is possible to obtain functionalized imidazole moieties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Imidazoles / chemistry*
  • Molecular Structure
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Stereoisomerism

Substances

  • Heterocyclic Compounds
  • Imidazoles
  • Pyridines