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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.

Authors
  • Kónya, Krisztina
  • Fekete, Szabolcs
  • Abrahám, Anita
  • Patonay, Tamás
Type
Published Article
Journal
Molecular Diversity
Publisher
Springer-Verlag
Publication Date
Feb 01, 2012
Volume
16
Issue
1
Pages
91–102
Identifiers
DOI: 10.1007/s11030-012-9360-7
PMID: 22307767
Source
Medline
License
Unknown

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.

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