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A practical flow synthesis of 1,2,3-triazoles
A robust and versatile protocol for synthesis of 1-monosubstituted and 1,4-disubstituted 1H-1,2,3-triazoles was established under continuous flow conditions using copper-on-charcoal as a heterogeneous catalyst. This methodology allowed for the synthesis of a diverse set of substituted 1,2,3-triazole...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9551675/ https://www.ncbi.nlm.nih.gov/pubmed/36320728 http://dx.doi.org/10.1039/d2ra04727f |
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author | Drelinkiewicz, Dawid Whitby, Richard J. |
author_facet | Drelinkiewicz, Dawid Whitby, Richard J. |
author_sort | Drelinkiewicz, Dawid |
collection | PubMed |
description | A robust and versatile protocol for synthesis of 1-monosubstituted and 1,4-disubstituted 1H-1,2,3-triazoles was established under continuous flow conditions using copper-on-charcoal as a heterogeneous catalyst. This methodology allowed for the synthesis of a diverse set of substituted 1,2,3-triazoles with good functional group tolerance and high yields. 2-Ynoic acids were also used as small-chain alkyne donors in a decarboxylation/cycloaddition cascade, allowing gaseous reagents to be bypassed, delivering desired triazoles in high yields. The developed methodology was used to synthesize an antiepileptic agent, rufinamide, which was obtained in 96% isolated yield. |
format | Online Article Text |
id | pubmed-9551675 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-95516752022-10-31 A practical flow synthesis of 1,2,3-triazoles Drelinkiewicz, Dawid Whitby, Richard J. RSC Adv Chemistry A robust and versatile protocol for synthesis of 1-monosubstituted and 1,4-disubstituted 1H-1,2,3-triazoles was established under continuous flow conditions using copper-on-charcoal as a heterogeneous catalyst. This methodology allowed for the synthesis of a diverse set of substituted 1,2,3-triazoles with good functional group tolerance and high yields. 2-Ynoic acids were also used as small-chain alkyne donors in a decarboxylation/cycloaddition cascade, allowing gaseous reagents to be bypassed, delivering desired triazoles in high yields. The developed methodology was used to synthesize an antiepileptic agent, rufinamide, which was obtained in 96% isolated yield. The Royal Society of Chemistry 2022-10-11 /pmc/articles/PMC9551675/ /pubmed/36320728 http://dx.doi.org/10.1039/d2ra04727f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Drelinkiewicz, Dawid Whitby, Richard J. A practical flow synthesis of 1,2,3-triazoles |
title | A practical flow synthesis of 1,2,3-triazoles |
title_full | A practical flow synthesis of 1,2,3-triazoles |
title_fullStr | A practical flow synthesis of 1,2,3-triazoles |
title_full_unstemmed | A practical flow synthesis of 1,2,3-triazoles |
title_short | A practical flow synthesis of 1,2,3-triazoles |
title_sort | practical flow synthesis of 1,2,3-triazoles |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9551675/ https://www.ncbi.nlm.nih.gov/pubmed/36320728 http://dx.doi.org/10.1039/d2ra04727f |
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