Tetrahedron, volume 70, issue 35, pages 5558-5568
1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties
Vasilieva Nadezhda V
2
,
Irtegova Irina G
2
,
Bagryanskaya Irina Yu.
2, 4
,
Shundrin Leonid A
2, 4
,
Sosnovskaya Zhanna Yu
1
,
Zibarev Andrey V.
2, 5, 6
,
1
5
Publication type: Journal Article
Publication date: 2014-09-01
Journal:
Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract A new general procedure for the selective synthesis of 1,2,5-thiadiazole 2-oxides (including fused derivatives) 8a,b,c,g,h from the reaction of vic-glyoximes with S2Cl2 and pyridine in acetonitrile was elaborated together with general procedure for the synthesis of 1,2,5-thiadiazoles 7a–i, 10, 12, and 14 from the same starting materials and reagents. Molecular structures of 3,4-dimethyl-1,2,5-thiadiazole 2-oxide 8a and [1,2,5]thiadiazolo[3,4-b]quinoxaline 10 were confirmed by single-crystal X-ray diffraction. Electrochemical properties of 1,2,5-thiadiazole 2-oxides 8 were studied by cyclic voltammetry and different behavior was observed for monocyclic and benzo-fused derivatives. With compounds 8g and 17, previously unknown deoxygenation of 2,1,3-benzothiadiazole 1-oxides was discovered by electrochemical reduction, and resulted 2,1,3-benzothiadiazoles 7g and 19 were detected in the forms of their radical anions by EPR spectroscopy combined with DFT calculations.
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1 publication, 4.17%
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1
2
3
4
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Konstantinova L. S. et al. 1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties // Tetrahedron. 2014. Vol. 70. No. 35. pp. 5558-5568.
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Konstantinova L. S., Knyazeva E. A., Obruchnikova N. V., Vasilieva N. V., Irtegova I. G., Nelyubina Y. V., Bagryanskaya I. Y., Shundrin L. A., Sosnovskaya Z. Yu., Zibarev A. V., Rakitin O. A. 1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties // Tetrahedron. 2014. Vol. 70. No. 35. pp. 5558-5568.
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TY - JOUR
DO - 10.1016/j.tet.2014.06.096
UR - https://doi.org/10.1016%2Fj.tet.2014.06.096
TI - 1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties
T2 - Tetrahedron
AU - Konstantinova, Lidia S.
AU - Obruchnikova, Natalia V.
AU - Vasilieva, Nadezhda V
AU - Irtegova, Irina G
AU - Bagryanskaya, Irina Yu.
AU - Shundrin, Leonid A
AU - Sosnovskaya, Zhanna Yu
AU - Zibarev, Andrey V.
AU - Knyazeva, Ekaterina A
AU - Nelyubina, Yulia V.
AU - Rakitin, Oleg A.
PY - 2014
DA - 2014/09/01 00:00:00
PB - Elsevier
SP - 5558-5568
IS - 35
VL - 70
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2014_Konstantinova,
author = {Lidia S. Konstantinova and Natalia V. Obruchnikova and Nadezhda V Vasilieva and Irina G Irtegova and Irina Yu. Bagryanskaya and Leonid A Shundrin and Zhanna Yu Sosnovskaya and Andrey V. Zibarev and Ekaterina A Knyazeva and Yulia V. Nelyubina and Oleg A. Rakitin},
title = {1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties},
journal = {Tetrahedron},
year = {2014},
volume = {70},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016%2Fj.tet.2014.06.096},
number = {35},
pages = {5558--5568},
doi = {10.1016/j.tet.2014.06.096}
}
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Konstantinova, Lidia S., et al. “1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties.” Tetrahedron, vol. 70, no. 35, Sep. 2014, pp. 5558-5568. https://doi.org/10.1016%2Fj.tet.2014.06.096.