α-Azido ketones. Part 7: synthesis of 1,4-disubstituted triazoles by the "click" reaction of various terminal acetylenes with phenacyl azides or α-azidobenzo(hetera)cyclanones

Mol Divers. 2012 Feb;16(1):91-102. doi: 10.1007/s11030-012-9360-7. Epub 2012 Feb 4.

Abstract

Copper(I)-catalyzed alkyne-azide 1,3-cycloaddition reaction (CuAAC, Sharpless-Meldal reaction) of various α-azido ketones such as substituted 2-azidoacetophenones, 2-azidobenzosuberone and 3-azido(thio)chromanones with terminal alkynes was studied. The reaction resulted in the formation of the expected 1,2,3-triazoles in moderate to good yields although the reactivity was somewhat lower than in the case of simple azides. Reaction of ethynylchromones as alkynes gave interesting dichromonoid systems bridged by a triazole unit.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Azides / chemical synthesis*
  • Azides / chemistry
  • Benzene / chemistry*
  • Chromones / chemistry*
  • Click Chemistry / methods*
  • Cyclization
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Alkynes
  • Azides
  • Chromones
  • Ketones
  • Triazoles
  • Benzene