Regioselective cobalt-catalyzed formation of bicyclic 3- and 4-aminopyridines

Org Lett. 2011 Apr 15;13(8):2030-3. doi: 10.1021/ol200417p. Epub 2011 Mar 17.

Abstract

Bimolecular cobalt-catalyzed [2 + 2 + 2] cycloadditions between yne-ynamides and nitriles afford bicyclic 3- or 4-aminopyridines in up to 100% yield. The high regioselectivity observed depends on the substitution pattern at the starting ynamide. Aminopyridines bearing TMS and Ts groups are efficiently deprotected in an orthogonal fashion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Aminopyridine / chemistry*
  • Aminopyridines / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Catalysis
  • Cobalt / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aminopyridines
  • Bridged Bicyclo Compounds, Heterocyclic
  • Cobalt
  • 3-aminopyridine
  • 4-Aminopyridine