Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties
AbstractA 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. View Full-Text
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Konstantinova, L.S.; Baranovsky, I.V.; Irtegova, I.G.; Bagryanskaya, I.Y.; Shundrin, L.A.; Zibarev, A.V.; Rakitin, O.A. Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties. Molecules 2016, 21, 596.
Konstantinova LS, Baranovsky IV, Irtegova IG, Bagryanskaya IY, Shundrin LA, Zibarev AV, Rakitin OA. Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties. Molecules. 2016; 21(5):596.Chicago/Turabian Style
Konstantinova, Lidia S.; Baranovsky, Ilia V.; Irtegova, Irina G.; Bagryanskaya, Irina Y.; Shundrin, Leonid A.; Zibarev, Andrey V.; Rakitin, Oleg A. 2016. "Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties." Molecules 21, no. 5: 596.
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