I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles

An iodine/DMSO catalyzed selective cyclization of N-tosylhydrazones with sulfur without adding external oxidant was developed for the synthesis of 4-aryl-1,2,3-thiadiazoles. In this reaction, oxidation of HI by using DMSO as dual oxidant and solvent is the key, which allowed the regeneration of I(2)...

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Autores principales: Li, Weiwei, Zhang, Jun, He, Jing, Xu, Liang, Vaccaro, Luigi, Liu, Ping, Gu, Yanlong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304252/
https://www.ncbi.nlm.nih.gov/pubmed/32596205
http://dx.doi.org/10.3389/fchem.2020.00466
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author Li, Weiwei
Zhang, Jun
He, Jing
Xu, Liang
Vaccaro, Luigi
Liu, Ping
Gu, Yanlong
author_facet Li, Weiwei
Zhang, Jun
He, Jing
Xu, Liang
Vaccaro, Luigi
Liu, Ping
Gu, Yanlong
author_sort Li, Weiwei
collection PubMed
description An iodine/DMSO catalyzed selective cyclization of N-tosylhydrazones with sulfur without adding external oxidant was developed for the synthesis of 4-aryl-1,2,3-thiadiazoles. In this reaction, oxidation of HI by using DMSO as dual oxidant and solvent is the key, which allowed the regeneration of I(2), ensuring thus the success of the synthesis. This protocol features by simple operation, high step-economy (one-pot fashion), broad substrate scope as well as scale-up ability.
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spelling pubmed-73042522020-06-26 I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles Li, Weiwei Zhang, Jun He, Jing Xu, Liang Vaccaro, Luigi Liu, Ping Gu, Yanlong Front Chem Chemistry An iodine/DMSO catalyzed selective cyclization of N-tosylhydrazones with sulfur without adding external oxidant was developed for the synthesis of 4-aryl-1,2,3-thiadiazoles. In this reaction, oxidation of HI by using DMSO as dual oxidant and solvent is the key, which allowed the regeneration of I(2), ensuring thus the success of the synthesis. This protocol features by simple operation, high step-economy (one-pot fashion), broad substrate scope as well as scale-up ability. Frontiers Media S.A. 2020-06-12 /pmc/articles/PMC7304252/ /pubmed/32596205 http://dx.doi.org/10.3389/fchem.2020.00466 Text en Copyright © 2020 Li, Zhang, He, Xu, Vaccaro, Liu and Gu. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Li, Weiwei
Zhang, Jun
He, Jing
Xu, Liang
Vaccaro, Luigi
Liu, Ping
Gu, Yanlong
I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles
title I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles
title_full I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles
title_fullStr I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles
title_full_unstemmed I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles
title_short I(2)/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles
title_sort i(2)/dmso-catalyzed transformation of n-tosylhydrazones to 1,2,3-thiadiazoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304252/
https://www.ncbi.nlm.nih.gov/pubmed/32596205
http://dx.doi.org/10.3389/fchem.2020.00466
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