Synthesis of pyrazoles via electrophilic cyclization

J Org Chem. 2011 Aug 19;76(16):6726-42. doi: 10.1021/jo201119e. Epub 2011 Jul 20.

Abstract

Electrophilic cyclizations of α,β-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. α,β-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated with molecular iodine in the presence of sodium bicarbonate, α,β-alkynic hydrazones underwent electrophilic cyclization to afford 4-iodopyrazoles in good to high yields. Iodocyclization was general for a wide range of α,β-alkynic hydrazones and tolerated the presence of aliphatic, aromatic, heteroaromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Electrons
  • Ferrous Compounds / chemistry
  • Hydrazones / chemistry*
  • Iodine / chemistry*
  • Molecular Structure
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry

Substances

  • Ferrous Compounds
  • Hydrazones
  • Pyrazoles
  • 4-iodopyrazole
  • Iodine