Tandem one-pot synthesis of polysubstituted pyridines using the Blaise reaction intermediate and 1,3-enynes

Org Lett. 2011 Dec 16;13(24):6390-3. doi: 10.1021/ol202691b. Epub 2011 Nov 10.

Abstract

A tandem one-pot method for the construction of a pyridine moiety with selective control of substitution patterns has been developed through the sequential reactions of nitrile with a Reformatsky reagent and 1,3-enyne involving regio- and chemoselective addition of the Blaise reaction intermediate to 1,3-enyne, followed by isomerization, cyclization, and an aromatization cascade.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Cyclization
  • Molecular Structure
  • Nitriles / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Nitriles
  • Pyridines