Me3SiCl-promoted Three-Component Coupling Reaction of a Functionalized Enamine, an Acetal, and an Alkyne: An Unprecedented Approach to the Synthesis of Tetrasubstituted Pyridines via a [3 + 2 + 1] Intermolecular Cyclization

J Org Chem. 2008 Sep 5;73(17):6905-8. doi: 10.1021/jo801090h. Epub 2008 Jul 29.

Abstract

We have identified a Me3SiCl-mediated three-component coupling reaction of a functionalized enamine, N,N-dimethylformamide diethyl acetal, and an internal alkyne having an electron-withdrawing group that produces 2,3,4,5-tetrasubstituted pyridine derivatives in good to excellent yields via a single-step reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry*
  • Alkynes / chemistry*
  • Amines / chemistry*
  • Crystallography, X-Ray
  • Cyclization
  • Dimethylformamide
  • Formamides / chemistry*
  • Models, Chemical
  • Pyridines / chemical synthesis*
  • Trimethylsilyl Compounds / chemistry*

Substances

  • Acetals
  • Alkynes
  • Amines
  • Formamides
  • Pyridines
  • Trimethylsilyl Compounds
  • Dimethylformamide