Synthesis of imidazo[1,2-a]pyridines: "water-mediated" hydroamination and silver-catalyzed aminooxygenation

J Org Chem. 2013 Feb 1;78(3):1266-72. doi: 10.1021/jo3025303. Epub 2013 Jan 16.

Abstract

Aqueous syntheses of methylimidazo[1,2-a]pyridines without any deliberate addition of catalyst are reported. Imidazo[1,2-a]pyrazine and imidazo[2,1-a]isoquinoline were also obtained in good yields under similar conditions. With acetonitrile as solvent, Ag-catalyzed intramolecular aminooxygenation produced imidazo[1,2-a]pyridine-3-carbaldehydes in moderate to good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Silver / chemistry*
  • Structure-Activity Relationship
  • Water

Substances

  • Imidazoles
  • Isoquinolines
  • Pyrazines
  • Pyridines
  • imidazo(1,2-a)pyrazine
  • imidazo(2,1-a)isoquinoline
  • Water
  • Silver