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K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes

An acid, transition-metal, and chromatography-free radical nitration/cyclisation of 2-alkynylthioanisoles or -selenoanisoles has been developed. This is the first example of the use of highly unstable 2-nitrovinyl radicals for C–S bond formation. This facile route efficiently produces 3-nitrobenzoth...

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Autores principales: Lu, Shi-Chao, Wu, Botao, Zhang, Shi-Peng, Gong, Ya-Ling, Xu, Shu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054014/
https://www.ncbi.nlm.nih.gov/pubmed/35518303
http://dx.doi.org/10.1039/d0ra03894f
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author Lu, Shi-Chao
Wu, Botao
Zhang, Shi-Peng
Gong, Ya-Ling
Xu, Shu
author_facet Lu, Shi-Chao
Wu, Botao
Zhang, Shi-Peng
Gong, Ya-Ling
Xu, Shu
author_sort Lu, Shi-Chao
collection PubMed
description An acid, transition-metal, and chromatography-free radical nitration/cyclisation of 2-alkynylthioanisoles or -selenoanisoles has been developed. This is the first example of the use of highly unstable 2-nitrovinyl radicals for C–S bond formation. This facile route efficiently produces 3-nitrobenzothiophenes and benzoselenophenes, which are difficult to access via classical methods. Density functional theory (DFT) calculations were carried out to probe the reaction mechanism. The resulting products were tested for their in vitro anti-tuberculosis activity, and compounds 2d and 2l showed significant activities against sensitive and drug-resistant strains.
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spelling pubmed-90540142022-05-04 K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes Lu, Shi-Chao Wu, Botao Zhang, Shi-Peng Gong, Ya-Ling Xu, Shu RSC Adv Chemistry An acid, transition-metal, and chromatography-free radical nitration/cyclisation of 2-alkynylthioanisoles or -selenoanisoles has been developed. This is the first example of the use of highly unstable 2-nitrovinyl radicals for C–S bond formation. This facile route efficiently produces 3-nitrobenzothiophenes and benzoselenophenes, which are difficult to access via classical methods. Density functional theory (DFT) calculations were carried out to probe the reaction mechanism. The resulting products were tested for their in vitro anti-tuberculosis activity, and compounds 2d and 2l showed significant activities against sensitive and drug-resistant strains. The Royal Society of Chemistry 2020-05-19 /pmc/articles/PMC9054014/ /pubmed/35518303 http://dx.doi.org/10.1039/d0ra03894f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Lu, Shi-Chao
Wu, Botao
Zhang, Shi-Peng
Gong, Ya-Ling
Xu, Shu
K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
title K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
title_full K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
title_fullStr K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
title_full_unstemmed K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
title_short K(2)S(2)O(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
title_sort k(2)s(2)o(8)-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054014/
https://www.ncbi.nlm.nih.gov/pubmed/35518303
http://dx.doi.org/10.1039/d0ra03894f
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