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Molecules 2016, 21(5), 596; doi:10.3390/molecules21050596

Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties

1
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia
2
Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia
3
N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia
4
Department of Natural Sciences, National Research University–Novosibirsk State University, 630090 Novosibirsk, Russia
5
Department of Chemistry, National Research University–Tomsk State University, 634050 Tomsk, Russia
*
Author to whom correspondence should be addressed.
Academic Editors: Panayiotis A. Koutentis and Andreas S. Kalogirou
Received: 28 March 2016 / Revised: 20 April 2016 / Accepted: 29 April 2016 / Published: 6 May 2016
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
View Full-Text   |   Download PDF [2307 KB, uploaded 6 May 2016]   |  

Abstract

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. View Full-Text
Keywords: fused 1,2,3-dithiazoles; synthesis; sulfur monochloride; X-ray diffraction; cyclic voltammetry fused 1,2,3-dithiazoles; synthesis; sulfur monochloride; X-ray diffraction; cyclic voltammetry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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