Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles

J Org Chem. 2021 Dec 3;86(23):17516-17522. doi: 10.1021/acs.joc.1c02309. Epub 2021 Nov 19.

Abstract

A three-component synthesis of 1,5-disubstituted 1,2,3-triazoles from α-acetyl-α-diazomethane sulfonamides, primary aliphatic amines, and aromatic aldehydes is presented. The 1,2,3-triazoles can be accessed in two alternative variants, depending on the substitutions in the sulfonamide portion of the diazo reagent. In one variant, intermediate 1,2,3-triazoline-4-sulfonamides are isolated chromatographically and then subjected to thermally promoted aromatization with elimination of sulfur(IV) oxide and amine. In the other variant, both chemical transformations take place in a single step conducted at room temperature.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes*
  • Amines
  • Metals
  • Sulfonamides
  • Triazoles*

Substances

  • Aldehydes
  • Amines
  • Metals
  • Sulfonamides
  • Triazoles