Iron-catalyzed cycloaddition reaction of diynes and cyanamides at room temperature

J Org Chem. 2013 Apr 5;78(7):3065-72. doi: 10.1021/jo400057t. Epub 2013 Feb 12.

Abstract

An iron-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and cyanamides at room temperature is reported. Highly substituted 2-aminopyridines were obtained in good to excellent yields with high regioselectivity. Insights toward the reaction process were investigated through in situ IR spectra and control experiments. In this iron-catalyzed cycloaddition reaction, the active iron species was generated only in the presence of both alkynes and nitriles. The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Aminopyridines / chemical synthesis*
  • Aminopyridines / chemistry
  • Catalysis
  • Cyanamide / chemistry*
  • Cyclization
  • Iron / chemistry*
  • Molecular Structure
  • Temperature*

Substances

  • Alkynes
  • Aminopyridines
  • Cyanamide
  • Iron
  • alpha-aminopyridine