An efficient synthesis of pyridoxal oxime derivatives under microwave irradiation

Molecules. 2014 Jun 6;19(6):7610-20. doi: 10.3390/molecules19067610.

Abstract

Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%-94%) were obtained in acetone in very short reaction times (3-5 min) as well as in the solvent-free procedure (42%-78%) in very short reaction times (7-10 min) too. Effective metodologies for the preparation of pyridoxal oxime quaternary salts, having the advantagies of being eco-friendly, easy to handle, and performed in shorter reactions time are presented. The structure of compound 7, in which a 4-fluorophenacyl moiety is bonded to the pyridinium ring nitrogen atom, was unequivocally confirmed by the single-crystal X-ray diffraction method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry*
  • Microwaves*
  • Molecular Structure
  • Pyridoxal / analogs & derivatives*
  • Pyridoxal / chemistry

Substances

  • Acetophenones
  • Pyridoxal
  • pyridoxaloxime
  • phenacyl bromide