American Chemical Society (ACS)
Organic Letters
,  volume 16 ,  issue 6 ,  pages 1582-1585

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

Publication type: Journal Article
Publication date: 2014-03-05
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
DOI:  10.1021/ol500125j
PubMed ID:  24593161
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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.
Found 
Found 
2 citations
Danilkina Natalia
44 publications,  625 citations
h-index: 14
Saint Petersburg State University
Saint Petersburg State University
Research interests
Bioorganic chemistry
Click chemistry
Heterocyclic compounds
Medicinal Chemistry
Organic Chemistry
1 citation
Beloglazkina Elena
DSc in Chemistry, professor
296 publications,  3 248 citations,  11 reviews
h-index: 29
Lomonosov Moscow State University
Lomonosov Moscow State University
1 citation
Luponosov Yuriy
🥼 🤝
DSc in Chemistry
113 publications,  2 526 citations,  13 reviews
h-index: 27
Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences
Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences
1 citation
Vil' Vera
PhD in Chemistry
86 publications,  1 967 citations,  3 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Organic Chemistry
1 citation
Yaremenko Ivan
PhD in Chemistry
60 publications,  1 567 citations,  5 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Organic Chemistry
1 citation
Gorbunova Yuliya
DSc in Chemistry, professor, full member of the Russian Academy of Sciences 
284 publications,  4 398 citations,  65 reviews
h-index: 34
Lomonosov Moscow State University
Lomonosov Moscow State University
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Lanthanides
Supramolecular chemistry
Tetrapyrrolic compounds
1 citation
Volcho Konstantin
DSc in Chemistry, professor of the Russian Academy of Sciences 
279 publications,  3 898 citations,  65 reviews
h-index: 31
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Osipov Sergey
DSc in Chemistry
138 publications,  2 739 citations,  3 reviews
h-index: 29
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
1 citation
Gazizov Almir
🥼
DSc in Chemistry
157 publications,  889 citations,  23 reviews
h-index: 14
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Heterocyclic compounds
Organic Chemistry
Organophosphorus chemistry
1 citation
Karasik Andrey
DSc in Chemistry, professor, associate member of the Russian Academy of Sciences 
224 publications,  2 599 citations
h-index: 26
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Luminescence
Phosphorus ligands
1 citation
Dotsenko Viktor
DSc in Chemistry, professor
244 publications,  2 741 citations,  2 reviews
h-index: 22
North Caucasus Federal University
North Caucasus Federal University
Kuban State University
Kuban State University
Research interests
Active methylene compounds
Biological activity
Heterocyclic compounds
Malononitrile
Selenoamides
Thioamides
1 citation
Zagidullin Almaz
🥼 🤝
PhD in Chemistry
81 publications,  884 citations
h-index: 17
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Asymmetric metal complex catalysis
Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
Coordination chemistry of phosphorus
Organoelement chemistry
Organophosphorus chemistry
Synthesis of chiral phosphorus-containing ligands
1 citation
Aksenov Aleksandr
🥼 🤝
DSc in Chemistry, professor
243 publications,  2 187 citations,  15 reviews
h-index: 24
North Caucasus Federal University
North Caucasus Federal University
Research interests
Medicinal Chemistry
Organic Chemistry
1 citation
Sosnovskikh Vyacheslav
DSc in Chemistry, professor
355 publications,  4 721 citations
h-index: 30
Ural Federal University
Ural Federal University
1 citation
Ilkin Vladimir
PhD in Chemistry
16 publications,  187 citations
h-index: 7
Ural Federal University
Ural Federal University
Research interests
Catalysis
Heterocyclic compounds
Organic Chemistry
Synthetic Organic Chemistry
1 citation
Krylov Igor
PhD in Chemistry
78 publications,  1 885 citations,  18 reviews
h-index: 25
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Green chemistry
Organic Chemistry
Organic electrochemistry
Organic synthesis
Photochemistry
Plant protection
1 citation
Tikhomirov Alexander
🥼 🤝
DSc in Chemistry, associate professor
59 publications,  920 citations
h-index: 17
Mendeleev University of Chemical Technology of Russia
Mendeleev University of Chemical Technology of Russia
Gause Institute of New Antibiotics
Gause Institute of New Antibiotics
Research interests
Medicinal Chemistry
1 citation
Ivanov Andrey
54 publications,  534 citations
h-index: 12
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Buev Evgeny
PhD in Chemistry
31 publications,  346 citations,  2 reviews
h-index: 9
Ural Federal University
Ural Federal University
Research interests
Chemistry of nitrogen-containing heterocycles
Organic Chemistry
Organic synthesis

Top-30

Journals

1
2
3
4
Journal of Organic Chemistry
Journal of Organic Chemistry, 4, 15.38%
Journal of Organic Chemistry
4 publications, 15.38%
Organic Letters
Organic Letters, 3, 11.54%
Organic Letters
3 publications, 11.54%
Tetrahedron Letters
Tetrahedron Letters, 2, 7.69%
Tetrahedron Letters
2 publications, 7.69%
European Journal of Organic Chemistry
European Journal of Organic Chemistry, 2, 7.69%
European Journal of Organic Chemistry
2 publications, 7.69%
Asian Journal of Organic Chemistry
Asian Journal of Organic Chemistry, 2, 7.69%
Asian Journal of Organic Chemistry
2 publications, 7.69%
Molecules
Molecules, 1, 3.85%
Molecules
1 publication, 3.85%
Tetrahedron
Tetrahedron, 1, 3.85%
Tetrahedron
1 publication, 3.85%
Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis, 1, 3.85%
Advanced Synthesis and Catalysis
1 publication, 3.85%
ChemCatChem
ChemCatChem, 1, 3.85%
ChemCatChem
1 publication, 3.85%
ChemInform
ChemInform, 1, 3.85%
ChemInform
1 publication, 3.85%
RSC Advances
RSC Advances, 1, 3.85%
RSC Advances
1 publication, 3.85%
Chemical Society Reviews
Chemical Society Reviews, 1, 3.85%
Chemical Society Reviews
1 publication, 3.85%
New Journal of Chemistry
New Journal of Chemistry, 1, 3.85%
New Journal of Chemistry
1 publication, 3.85%
Synthetic Communications
Synthetic Communications, 1, 3.85%
Synthetic Communications
1 publication, 3.85%
ChemistrySelect
ChemistrySelect, 1, 3.85%
ChemistrySelect
1 publication, 3.85%
Organic Reaction Mechanisms
Organic Reaction Mechanisms, 1, 3.85%
Organic Reaction Mechanisms
1 publication, 3.85%
Russian Chemical Reviews
Russian Chemical Reviews, 1, 3.85%
Russian Chemical Reviews
1 publication, 3.85%
Materials Today Chemistry
Materials Today Chemistry, 1, 3.85%
Materials Today Chemistry
1 publication, 3.85%
1
2
3
4

Publishers

1
2
3
4
5
6
7
8
9
Wiley
Wiley, 9, 34.62%
Wiley
9 publications, 34.62%
American Chemical Society (ACS)
American Chemical Society (ACS), 7, 26.92%
American Chemical Society (ACS)
7 publications, 26.92%
Elsevier
Elsevier, 4, 15.38%
Elsevier
4 publications, 15.38%
Royal Society of Chemistry (RSC)
Royal Society of Chemistry (RSC), 3, 11.54%
Royal Society of Chemistry (RSC)
3 publications, 11.54%
MDPI
MDPI, 1, 3.85%
MDPI
1 publication, 3.85%
Taylor & Francis
Taylor & Francis, 1, 3.85%
Taylor & Francis
1 publication, 3.85%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 3.85%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 3.85%
1
2
3
4
5
6
7
8
9
  • We do not take into account publications without a DOI.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
26
Share
Cite this
GOST |
Cite this
GOST Copy
Gulevskaya A. V. et al. Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision // Organic Letters. 2014. Vol. 16. No. 6. pp. 1582-1585.
GOST all authors (up to 50) Copy
Gulevskaya A. V., Tyaglivy A. S., Pozharskii A. F., Nelina Nemtseva J. I., Steglenko D. V. Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision // Organic Letters. 2014. Vol. 16. No. 6. pp. 1582-1585.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/ol500125j
UR - https://doi.org/10.1021/ol500125j
TI - Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision
T2 - Organic Letters
AU - Gulevskaya, Anna V
AU - Tyaglivy, Alexander S
AU - Pozharskii, Alexander F.
AU - Nelina Nemtseva, Julia I
AU - Steglenko, Dmitry V.
PY - 2014
DA - 2014/03/05
PB - American Chemical Society (ACS)
SP - 1582-1585
IS - 6
VL - 16
PMID - 24593161
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2014_Gulevskaya,
author = {Anna V Gulevskaya and Alexander S Tyaglivy and Alexander F. Pozharskii and Julia I Nelina Nemtseva and Dmitry V. Steglenko},
title = {Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision},
journal = {Organic Letters},
year = {2014},
volume = {16},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ol500125j},
number = {6},
pages = {1582--1585},
doi = {10.1021/ol500125j}
}
MLA
Cite this
MLA Copy
Gulevskaya, Anna V., et al. “Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision.” Organic Letters, vol. 16, no. 6, Mar. 2014, pp. 1582-1585. https://doi.org/10.1021/ol500125j.