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Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones
A sequential Rh(III)-catalyzed C-H activation/annulation of N-hydroxybenzamides with propargylic acetates leading to the formation of NH-free isoquinolones is described. This reaction proceeds through a sequential C-H activation/alkyne insertion/intramolecular annulation/N-O bond cleavage procedure,...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9740102/ https://www.ncbi.nlm.nih.gov/pubmed/36500644 http://dx.doi.org/10.3390/molecules27238553 |
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author | Fang, Taibei Zhang, Shiwen Ye, Qingqing Kong, Shuwen Yang, Tingting Tang, Kaijie He, Xinwei Shang, Yongjia |
author_facet | Fang, Taibei Zhang, Shiwen Ye, Qingqing Kong, Shuwen Yang, Tingting Tang, Kaijie He, Xinwei Shang, Yongjia |
author_sort | Fang, Taibei |
collection | PubMed |
description | A sequential Rh(III)-catalyzed C-H activation/annulation of N-hydroxybenzamides with propargylic acetates leading to the formation of NH-free isoquinolones is described. This reaction proceeds through a sequential C-H activation/alkyne insertion/intramolecular annulation/N-O bond cleavage procedure, affording a broad spectrum of products with diverse substituents in moderate-to-excellent yields. Notably, this protocol features the simultaneous formation of two new C-C/C-N bonds and one heterocycle in one pot with the release of water as the sole byproduct. |
format | Online Article Text |
id | pubmed-9740102 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-97401022022-12-11 Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones Fang, Taibei Zhang, Shiwen Ye, Qingqing Kong, Shuwen Yang, Tingting Tang, Kaijie He, Xinwei Shang, Yongjia Molecules Article A sequential Rh(III)-catalyzed C-H activation/annulation of N-hydroxybenzamides with propargylic acetates leading to the formation of NH-free isoquinolones is described. This reaction proceeds through a sequential C-H activation/alkyne insertion/intramolecular annulation/N-O bond cleavage procedure, affording a broad spectrum of products with diverse substituents in moderate-to-excellent yields. Notably, this protocol features the simultaneous formation of two new C-C/C-N bonds and one heterocycle in one pot with the release of water as the sole byproduct. MDPI 2022-12-05 /pmc/articles/PMC9740102/ /pubmed/36500644 http://dx.doi.org/10.3390/molecules27238553 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Fang, Taibei Zhang, Shiwen Ye, Qingqing Kong, Shuwen Yang, Tingting Tang, Kaijie He, Xinwei Shang, Yongjia Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones |
title | Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones |
title_full | Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones |
title_fullStr | Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones |
title_full_unstemmed | Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones |
title_short | Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones |
title_sort | rh-catalyzed cascade c-h activation/annulation of n-hydroxybenzamides and propargylic acetates for modular access to isoquinolones |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9740102/ https://www.ncbi.nlm.nih.gov/pubmed/36500644 http://dx.doi.org/10.3390/molecules27238553 |
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