One-Step Synthesis of Sulfonamides from N-Tosylhydrazones

Org Lett. 2016 Feb 5;18(3):508-11. doi: 10.1021/acs.orglett.5b03545. Epub 2016 Jan 15.

Abstract

The first described reaction between N-tosylhydrazone and SO2 is reported to provide alkyl sulfonamides in the presence of various amines. In this procedurally simple method, hydrazones of both unsaturated aldehydes and ketones proceed in moderate to excellent yields. Primary and secondary aliphatic amines are accommodated in this reaction, which provides a novel route to sulfonamides.

MeSH terms

  • Aldehydes / chemistry
  • Amines / chemistry
  • Catalysis
  • Hydrazones / chemistry*
  • Ketones / chemistry
  • Molecular Structure
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfur Dioxide / chemistry

Substances

  • Aldehydes
  • Amines
  • Hydrazones
  • Ketones
  • Sulfonamides
  • Sulfur Dioxide