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,...

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Detalles Bibliográficos
Autores principales: Fang, Taibei, Zhang, Shiwen, Ye, Qingqing, Kong, Shuwen, Yang, Tingting, Tang, Kaijie, He, Xinwei, Shang, Yongjia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
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.
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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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