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

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...

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Autores principales: Konstantinova, Lidia S., Baranovsky, Ilia V., Strunyasheva, Vlada V., Kalogirou, Andreas S., Popov, Vadim V., Lyssenko, Konstantin A., Koutentis, Panayiotis A., Rakitin, Oleg A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099702/
https://www.ncbi.nlm.nih.gov/pubmed/29795048
http://dx.doi.org/10.3390/molecules23061257
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author Konstantinova, Lidia S.
Baranovsky, Ilia V.
Strunyasheva, Vlada V.
Kalogirou, Andreas S.
Popov, Vadim V.
Lyssenko, Konstantin A.
Koutentis, Panayiotis A.
Rakitin, Oleg A.
author_facet Konstantinova, Lidia S.
Baranovsky, Ilia V.
Strunyasheva, Vlada V.
Kalogirou, Andreas S.
Popov, Vadim V.
Lyssenko, Konstantin A.
Koutentis, Panayiotis A.
Rakitin, Oleg A.
author_sort Konstantinova, Lidia S.
collection PubMed
description 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.
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spelling pubmed-60997022018-11-13 The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles Konstantinova, Lidia S. Baranovsky, Ilia V. Strunyasheva, Vlada V. Kalogirou, Andreas S. Popov, Vadim V. Lyssenko, Konstantin A. Koutentis, Panayiotis A. Rakitin, Oleg A. Molecules Article 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. MDPI 2018-05-24 /pmc/articles/PMC6099702/ /pubmed/29795048 http://dx.doi.org/10.3390/molecules23061257 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Konstantinova, Lidia S.
Baranovsky, Ilia V.
Strunyasheva, Vlada V.
Kalogirou, Andreas S.
Popov, Vadim V.
Lyssenko, Konstantin A.
Koutentis, Panayiotis A.
Rakitin, Oleg A.
The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
title The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
title_full The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
title_fullStr The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
title_full_unstemmed The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
title_short The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
title_sort conversion of 5,5′-bi(1,2,3-dithiazolylidenes) into isothiazolo[5,4-d]isothiazoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099702/
https://www.ncbi.nlm.nih.gov/pubmed/29795048
http://dx.doi.org/10.3390/molecules23061257
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