1,2,5-Thiadiazole 2-oxides: selective synthesis, structural characterization, and electrochemical properties

1,2,5-Thiadiazole 2-oxides: selective synthesis, structural characterization, and electrochemical properties Full article

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 2014, Volume: 70, Number: 35, Pages: 5558-5568 Pages count : DOI: 10.1016/j.tet.2014.06.096

Tags

1,2,5-Thiadiazole 2-oxides; Sulfur monochloride; X-ray diffraction; Cyclic voltammetry; EPR spectroscopy; DFT calculations

Authors

Konstantinova Lidia S. ¹ , Knyazeva Ekaterina A. ¹ , Obruchnikova Natalia V. ¹ , Vasilieva Nadezhda V. ² , Irtegova Irina G. ² , Nelyubina Yulia V. ³ , Bagryanskaya Irina Yu ^2,4 , Shundrin Leonid A. ^2,4 , Sosnovskaya Zhanna Yu ¹ , Zibarev Andrey V. ^2,5,6 , Rakitin Oleg A. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
2	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
4	(Данные Web of science) Novosibirsk State Univ, Natl Res Univ, Dept Nat Sci, Novosibirsk 630090, Russia
5	(Данные Web of science) Novosibirsk State Univ, Natl Res Univ, Dept Phys, Novosibirsk 630090, Russia
6	(Данные Web of science) Tomsk State Univ, Natl Res Univ, Dept Chem, Tomsk 634050, Russia

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. (C) 2014 Elsevier Ltd. All rights reserved.

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.Y. , Zibarev A.V. , Rakitin O.A.
1,2,5-Thiadiazole 2-oxides: selective synthesis, structural characterization, and electrochemical properties
Tetrahedron. 2014. V.70. N35. P.5558-5568. DOI: 10.1016/j.tet.2014.06.096 WOS Scopus РИНЦ

Published print:

Sep 1, 2014

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