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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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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. |
format | Online Article Text |
id | pubmed-9054014 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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