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Molecules 2018, 23(6), 1257; https://doi.org/10.3390/molecules23061257

The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles

1
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia
2
Nanotechnology Education and Research Center, South Ural State University, Chelyabinsk 454080, Russia
3
Department of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, Cyprus
4
Department of Life Sciences, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, P.O. Box 22006, Nicosia 1516, Cyprus
5
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991, Russia
*
Authors to whom correspondence should be addressed.
Received: 15 May 2018 / Revised: 21 May 2018 / Accepted: 24 May 2018 / Published: 24 May 2018
(This article belongs to the Special Issue Recent Advances in Nitrogen-Containing Aromatic Heterocycles)
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Abstract

Thermolysis of 4,4′-dichloro-, 4,4′-diaryl-, and 4,4′-di(thien-2-yl)-5,5′-bi(1,2,3-dithiazol-ylidenes) affords the respective 3,6-dichloro-, 3,6-diaryl- and 3,6-di(thien-2-yl)isothiazolo[5,4-d]-isothiazoles in low to high yields. The transformation of the 4,4′-diaryl- and 4,4′-di(thien-2-yl)-5,5′-bi(1,2,3-dithiazolylidenes) occurs at lower temperatures in the presence of the thiophiles triphenylphosphine or tetraethylammonium iodide. Optimized reaction conditions and a mechanistic rationale for the thiophile-mediated ring transformation are presented. View Full-Text
Keywords: sulfur-nitrogen heterocycles; dithiazoles; isothiazoles; ring transformation sulfur-nitrogen heterocycles; dithiazoles; isothiazoles; ring transformation
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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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Konstantinova, L.S.; Baranovsky, I.V.; Strunyasheva, V.V.; Kalogirou, A.S.; Popov, V.V.; Lyssenko, K.A.; Koutentis, P.A.; Rakitin, O.A. The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles. Molecules 2018, 23, 1257.

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