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

Krisztina Kónya, Szabolcs Fekete, Anita Ábrahám, Tamás Patonay

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8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)91-102
Number of pages12
JournalMolecular Diversity
Volume16
Issue number1
DOIs
Publication statusPublished - Feb 1 2012

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Keywords

  • 1,2,3-Triazole
  • 1,3-Dipolar cycloaddition
  • Alkyne
  • Chromanone
  • α-Azido ketone

ASJC Scopus subject areas

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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