Ι₂-mediated amination/cyclization of ketones with 2-aminopyridines under high-speed ball milling: solvent- and metal-free synthesis of 2,3-substituted imidazo[1,2-a]pyridines and zolimidine

Mol Divers. 2016 Aug;20(3):659-66. doi: 10.1007/s11030-016-9666-y. Epub 2016 Mar 14.

Abstract

Under solvent-free high-speed ball milling, an I[Formula: see text]-promoted condensation/cyclization of easily available methyl ketones or 1,3-dicarbonyl compounds with 2-aminopyridines has been developed, which allows the quick assembly of 2,3-substituted imidazo[1,2-a]pyridines (IPs) with broad molecular diversity, including the antiulcer drug zolimidine. The advantages of high yields, good functional group compatibility, short reaction time (within 90 min), free use of heating, solvent and metal, employment of cheap starting materials, and simple work-up procedure make this protocol a very efficient alternative to traditional synthesis of IPs.

Keywords: Cyclization; Heterocycle synthesis; High-speed ball milling; Imidazo[1, 2-a]pyridines; Iodine; Metal-free; Solvent-free; Zolimidine.

MeSH terms

  • Amination
  • Catalysis
  • Cyclization
  • Imidazoles / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Pyridines / chemistry*
  • Solvents

Substances

  • Imidazoles
  • Ketones
  • Pyridines
  • Solvents
  • zolimidine