Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X‑ray Data and Structure Revision

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 mad...

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Bibliographic Details
Published in:Organic letters 2014-03, Vol.16 (6), p.1582-1585
Main Authors: Gulevskaya, Anna V, Tyaglivy, Alexander S, Pozharskii, Alexander F, Nelina-Nemtseva, Julia I, Steglenko, Dmitry V
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Cyclization
Enediynes - chemistry
Models, Molecular
Molecular Conformation
Molecular Structure
Pyridines
Sodium Azide - chemistry
Triazoles - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500125j