Tetrahedron p. 5558 - 5568 (2014)
Update date:2022-08-04
Topics:
Konstantinova, Lidia S.
Knyazeva, Ekaterina A.
Obruchnikova, Natalia V.
Vasilieva, Nadezhda V.
Irtegova, Irina G.
Nelyubina, Yulia V.
Bagryanskaya, Irina Yu.
Shundrin, Leonid A.
Sosnovskaya, Zhanna Yu.
Zibarev, Andrey V.
Rakitin, Oleg A.
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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