Fused 1,2,3-dithiazoles: convenient synthesis, structural characterization, and electrochemical properties

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DOI Доступ к ресурсу на сайте издателя			10.3390/molecules21050596

Title: Fused 1,2,3-dithiazoles: convenient synthesis, structural characterization, and electrochemical properties
Creator: Konstantinova, Lidia S
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Irtegova, Irina G.
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Bagryanskaya, Irina Y.
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Shundrin, Leonid A.
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Zibarev, Andrey V.
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Rakitin, Oleg A.
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Baranovsky, Ilia V.
Date: 2016
DOI: 10.3390/molecules21050596
Description: A new general protocol for synthesis of fused 1,2,3-dithiazoles by the reaction of cyclic oximes with S2Cl2 and pyridine in acetonitrile has been developed. The target 1,2,3-dithiazoles fused with various carbocycles, such as indene, naphthalenone, cyclohexadienone, cyclopentadiene, and benzoannulene, were selectively obtained in low to high yields. In most cases, the hetero ring-closure was accompanied by chlorination of the carbocyclic moieties. With naphthalenone derivatives, a novel dithiazole rearrangement (15→13) featuring unexpected movement of the dithiazole ring from α- to β-position, with respect to keto group, was discovered. Molecular structure of 4-chloro-5H-naphtho[1,2-d][1,2,3]dithiazol-5-one 13 was confirmed by single-crystal X-ray diffraction. Electrochemical properties of 13 were studied by cyclic voltammetry and a complex behavior was observed, most likely including hydrodechlorination at a low potential.

Created: 27-03-2017

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Химический факультет Fused 1,2,3-dithiazoles: convenient synthesis, structural characterization, and electrochemical properties