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

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

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2016, Volume: 21, Number: 5, Article number : 596, Pages count : DOI: 10.3390/molecules21050596

Tags

fused 1,2,3-dithiazoles; synthesis; sulfur monochloride; X-ray diffraction; cyclic voltammetry

Authors

Konstantinova Lidia S. ^1,2 , Baranovsky Ilia V. ¹ , Irtegova Irina G. ³ , Bagryanskaya Irina Y. ^3,4 , Shundrin Leonid A. ^3,4 , Zibarev Andrey V. ^3,5 , Rakitin Oleg A. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
2	(Данные Web of science) South Ural State Univ, Nanotechnol Educ & Res Ctr, Chelyabinsk 454080, Russia
3	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
4	(Данные Web of science) Natl Res Univ Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia
5	(Данные Web of science) Natl Res Univ Tomsk State Univ, Dept Chem, Tomsk 634050, Russia

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 alpha- to beta-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.

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. V.21. N5. 596 . DOI: 10.3390/molecules21050596 WOS Scopus РИНЦ

Full text from publisher

Published online:

May 6, 2016

Web of science	WOS:000380241600060
Scopus	2-s2.0-85016401823
Elibrary	41779020
OpenAlex	W2345431354