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Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin
Bromoaryl compounds have attracted great attention in organic chemistry, especially for the synthesis of pharmaceutical intermediates. Herein, we demonstrated a novel and efficient bromination protocol of indazoles via C–H bond cleavage to give site-specific 3-bromide products that could be further...
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/PMC9773018/ https://www.ncbi.nlm.nih.gov/pubmed/36605629 http://dx.doi.org/10.1039/d2ra06867b |
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author | Ying, Shengneng Liu, Xingru Guo, Tao Li, Xuan Zhou, Min Wang, Xia Zhu, Mengxue Jiang, Hongmei Gui, Qing-Wen |
author_facet | Ying, Shengneng Liu, Xingru Guo, Tao Li, Xuan Zhou, Min Wang, Xia Zhu, Mengxue Jiang, Hongmei Gui, Qing-Wen |
author_sort | Ying, Shengneng |
collection | PubMed |
description | Bromoaryl compounds have attracted great attention in organic chemistry, especially for the synthesis of pharmaceutical intermediates. Herein, we demonstrated a novel and efficient bromination protocol of indazoles via C–H bond cleavage to give site-specific 3-bromide products that could be further employed as synthetic blocks to prepare drugs. The reaction used DBDMH as a bromine source, tolerated a wide range of indazoles, and finished in 30 min under mild, ultrasound-assisted conditions. Besides, preliminary mechanistic studies revealed that this approach was not a radical process. |
format | Online Article Text |
id | pubmed-9773018 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-97730182023-01-04 Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin Ying, Shengneng Liu, Xingru Guo, Tao Li, Xuan Zhou, Min Wang, Xia Zhu, Mengxue Jiang, Hongmei Gui, Qing-Wen RSC Adv Chemistry Bromoaryl compounds have attracted great attention in organic chemistry, especially for the synthesis of pharmaceutical intermediates. Herein, we demonstrated a novel and efficient bromination protocol of indazoles via C–H bond cleavage to give site-specific 3-bromide products that could be further employed as synthetic blocks to prepare drugs. The reaction used DBDMH as a bromine source, tolerated a wide range of indazoles, and finished in 30 min under mild, ultrasound-assisted conditions. Besides, preliminary mechanistic studies revealed that this approach was not a radical process. The Royal Society of Chemistry 2022-12-22 /pmc/articles/PMC9773018/ /pubmed/36605629 http://dx.doi.org/10.1039/d2ra06867b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Ying, Shengneng Liu, Xingru Guo, Tao Li, Xuan Zhou, Min Wang, Xia Zhu, Mengxue Jiang, Hongmei Gui, Qing-Wen Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin |
title | Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin |
title_full | Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin |
title_fullStr | Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin |
title_full_unstemmed | Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin |
title_short | Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin |
title_sort | ultrasound-assisted bromination of indazoles at the c3 position with dibromohydantoin |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9773018/ https://www.ncbi.nlm.nih.gov/pubmed/36605629 http://dx.doi.org/10.1039/d2ra06867b |
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