Electrochemical synthesis of sulfonamide derivatives based on the oxidation of 2,5-diethoxy-4-morpholinoaniline in the presence of arylsulfinic acids

J Org Chem. 2014 Jul 3;79(13):6326-9. doi: 10.1021/jo500812d. Epub 2014 Jun 19.

Abstract

Some new sulfonamide derivatives were synthesized in aqueous solutions via anodic oxidation of 2,5-diethoxy-4-morpholinoaniline in the presence of arylsulfinic acids using a commercial carbon anode. In addition, the formation mechanism of the products was discussed. The obtained data show that the electrogenerated quinone diimine undergoes a Michael-type addition reaction with arylsulfinic acids to yield the respective sulfonamide derivatives. In this work, two different types of products (mono- and disulfone derivatives) in the same precursor could be isolated just by controlling the exerted potentials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Electrochemistry
  • Molecular Structure
  • Morpholines / chemistry*
  • Oxidation-Reduction
  • Sulfides / chemistry*
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry

Substances

  • Aniline Compounds
  • Morpholines
  • Sulfides
  • Sulfonamides
  • Sulfones
  • 2,5-diethoxy-4-morpholinoaniline