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Heterocyclization of enediynes promoted by sodium azide: a case of ambiguity of X-ray data and structure revision.

Authors
  • Gulevskaya, Anna V1
  • Tyaglivy, Alexander S
  • Pozharskii, Alexander F
  • Nelina-Nemtseva, Julia I
  • Steglenko, Dmitry V
  • 1 Department of Organic Chemistry, Southern Federal University , Zorge 7, Rostov-on-Don 344090, Russian Federation. , (Russia)
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Mar 21, 2014
Volume
16
Issue
6
Pages
1582–1585
Identifiers
DOI: 10.1021/ol500125j
PMID: 24593161
Source
Medline
License
Unknown

Abstract

It has been shown that contrary to the literature data the tandem cyclization of (Z)-1-aryl-3-hexen-1,5-diynes promoted by sodium azide results in the formation of the corresponding [1,2,3]triazolo[1,5-a]pyridines, not 1H-benzotriazole derivatives. Apparently, incorrect structure elucidation made by previous investigators originates from misinterpretation of X-ray data. A number of new transformations of this type as well as X-ray and NMR experiments are discussed.

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