Unprecedented catalytic activity of Fe(NO3)3·9H2O: regioselective synthesis of 2-nitroimidazopyridines via oxidative amination

Org Lett. 2014 Sep 5;16(17):4630-3. doi: 10.1021/ol502218u. Epub 2014 Aug 20.

Abstract

A unique iron-catalyzed oxidative diamination of nitroalkene with 2-aminopyridine for the synthesis of 2-nitro-3-arylimidazo[1,2-a]pyridines with complete regioselectivity has been achieved under mild and aerobic reaction conditions. This is the first method for the synthesis of 2-nitroimidazo[1,2-a]pyridines. These scaffolds were also synthesized directly from styrenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Amination
  • Aminopyridines / chemical synthesis*
  • Aminopyridines / chemistry
  • Catalysis
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Iron / chemistry*
  • Molecular Structure
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry
  • Oxidation-Reduction
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Stereoisomerism
  • Styrenes / chemistry

Substances

  • Alkenes
  • Aminopyridines
  • Imidazoles
  • Nitro Compounds
  • Pyridines
  • Styrenes
  • Iron
  • alpha-aminopyridine