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Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives

The article is devoted to heterocyclization of bis(2-chloroprop-2-en-1-yl)sulfide which proceeds in hydrazine hydrate–alkali medium and leads to formation of thiophene and pyrrole derivatives: previously described 4,5,9,10-tetrahydrocycloocta[1,2-c;5,8-c’]dithiophene, as well as unknown hydrazone of...

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Autores principales: Rozentsveig, Igor B., Nikonova, Valentina S., Manuilov, Victor V., Ushakov, Igor A., Borodina, Tatyana N., Smirnov, Vladimir I., Korchevin, Nikolay A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609936/
https://www.ncbi.nlm.nih.gov/pubmed/36296380
http://dx.doi.org/10.3390/molecules27206785
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author Rozentsveig, Igor B.
Nikonova, Valentina S.
Manuilov, Victor V.
Ushakov, Igor A.
Borodina, Tatyana N.
Smirnov, Vladimir I.
Korchevin, Nikolay A.
author_facet Rozentsveig, Igor B.
Nikonova, Valentina S.
Manuilov, Victor V.
Ushakov, Igor A.
Borodina, Tatyana N.
Smirnov, Vladimir I.
Korchevin, Nikolay A.
author_sort Rozentsveig, Igor B.
collection PubMed
description The article is devoted to heterocyclization of bis(2-chloroprop-2-en-1-yl)sulfide which proceeds in hydrazine hydrate–alkali medium and leads to formation of thiophene and pyrrole derivatives: previously described 4,5,9,10-tetrahydrocycloocta[1,2-c;5,8-c’]dithiophene, as well as unknown hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one and 1-amino-2-(propynylsulfanylpropenylsulfanyl)-3,5-dimethylpyrrole. Tentative mechanisms for the formation of the heterocyclic products are discussed. Obtained hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one was used for the synthesis of a range of azine derivatives and in oxidation process with SeO(2). The found reactions open up expedient approaches to the formation of various hardly accessible thiophene and pyrrole compounds from 2,3-dichloropropene and elemental sulfur as starting reagents.
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spelling pubmed-96099362022-10-28 Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives Rozentsveig, Igor B. Nikonova, Valentina S. Manuilov, Victor V. Ushakov, Igor A. Borodina, Tatyana N. Smirnov, Vladimir I. Korchevin, Nikolay A. Molecules Article The article is devoted to heterocyclization of bis(2-chloroprop-2-en-1-yl)sulfide which proceeds in hydrazine hydrate–alkali medium and leads to formation of thiophene and pyrrole derivatives: previously described 4,5,9,10-tetrahydrocycloocta[1,2-c;5,8-c’]dithiophene, as well as unknown hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one and 1-amino-2-(propynylsulfanylpropenylsulfanyl)-3,5-dimethylpyrrole. Tentative mechanisms for the formation of the heterocyclic products are discussed. Obtained hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one was used for the synthesis of a range of azine derivatives and in oxidation process with SeO(2). The found reactions open up expedient approaches to the formation of various hardly accessible thiophene and pyrrole compounds from 2,3-dichloropropene and elemental sulfur as starting reagents. MDPI 2022-10-11 /pmc/articles/PMC9609936/ /pubmed/36296380 http://dx.doi.org/10.3390/molecules27206785 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Rozentsveig, Igor B.
Nikonova, Valentina S.
Manuilov, Victor V.
Ushakov, Igor A.
Borodina, Tatyana N.
Smirnov, Vladimir I.
Korchevin, Nikolay A.
Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives
title Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives
title_full Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives
title_fullStr Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives
title_full_unstemmed Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives
title_short Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives
title_sort heterocyclization of bis(2-chloroprop-2-en-1-yl)sulfide in hydrazine hydrate–koh: synthesis of thiophene and pyrrole derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609936/
https://www.ncbi.nlm.nih.gov/pubmed/36296380
http://dx.doi.org/10.3390/molecules27206785
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