Mechanistic investigation on the formation of indolizines from 2-enynylpyridines

Org Lett. 2009 Nov 5;11(21):4802-5. doi: 10.1021/ol901760a.

Abstract

2,3,7-Trisubstituted indolizines were obtained from E- or Z-2-enynyl-4-substituted pyridines. The mechanistic pathway involves a base-catalyzed double-bond isomerization, if the E-isomer is the starting material, followed by a concerted pseudocoarctate cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Indolizines / chemical synthesis*
  • Indolizines / chemistry
  • Molecular Structure
  • Pyridines / chemistry*
  • Stereoisomerism

Substances

  • Indolizines
  • Pyridines