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&...

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Main Authors:	Lidia S. Konstantinova, Ilia V. Baranovsky, Vlada V. Strunyasheva, Andreas S. Kalogirou, Vadim V. Popov, Konstantin A. Lyssenko, Panayiotis A. Koutentis, Oleg A. Rakitin
Format:	Article
Language:	English
Published:	MDPI AG 2018-05-01
Series:	Molecules
Subjects:	sulfur-nitrogen heterocycles dithiazoles isothiazoles ring transformation
Online Access:	http://www.mdpi.com/1420-3049/23/6/1257

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spelling	doaj-e0679c1d6c304d5fa0517c554af23ea42020-11-25T01:48:28ZengMDPI AGMolecules1420-30492018-05-01236125710.3390/molecules23061257molecules23061257The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazolesLidia S. Konstantinova0Ilia V. Baranovsky1Vlada V. Strunyasheva2Andreas S. Kalogirou3Vadim V. Popov4Konstantin A. Lyssenko5Panayiotis A. Koutentis6Oleg A. Rakitin7N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, RussiaDepartment of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, CyprusNanotechnology Education and Research Center, South Ural State University, Chelyabinsk 454080, RussiaA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991, RussiaDepartment of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, CyprusN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, RussiaThermolysis 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.http://www.mdpi.com/1420-3049/23/6/1257sulfur-nitrogen heterocyclesdithiazolesisothiazolesring transformation
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Lidia S. Konstantinova Ilia V. Baranovsky Vlada V. Strunyasheva Andreas S. Kalogirou Vadim V. Popov Konstantin A. Lyssenko Panayiotis A. Koutentis Oleg A. Rakitin
spellingShingle	Lidia S. Konstantinova Ilia V. Baranovsky Vlada V. Strunyasheva Andreas S. Kalogirou Vadim V. Popov Konstantin A. Lyssenko Panayiotis A. Koutentis Oleg A. Rakitin The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles Molecules sulfur-nitrogen heterocycles dithiazoles isothiazoles ring transformation
author_facet	Lidia S. Konstantinova Ilia V. Baranovsky Vlada V. Strunyasheva Andreas S. Kalogirou Vadim V. Popov Konstantin A. Lyssenko Panayiotis A. Koutentis Oleg A. Rakitin
author_sort	Lidia S. Konstantinova
title	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_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_sort	conversion of 5,5′-bi(1,2,3-dithiazolylidenes) into isothiazolo[5,4-d]isothiazoles
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2018-05-01
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.
topic	sulfur-nitrogen heterocycles dithiazoles isothiazoles ring transformation
url	http://www.mdpi.com/1420-3049/23/6/1257
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The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles

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