Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles

A palladium(ii)-catalyzed intramolecular oxidative aza-Wacker-type reaction of vinyl cyclopropanecarboxamides to access a series of conformationally restricted highly substituted aza[3.1.0]bicycles is reported. The transformation proceeded through a typical aza-Wacker reaction mechanism to forge a n...

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Autores principales: Li, Mengjuan, Li, Jingya, Zhang, Zhiguo, Chen, Liming, Ma, Nana, Liu, Qingfeng, Zhang, Xingjie, Zhang, Guisheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10493647/
https://www.ncbi.nlm.nih.gov/pubmed/37701284
http://dx.doi.org/10.1039/d3ra05440c
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author Li, Mengjuan
Li, Jingya
Zhang, Zhiguo
Chen, Liming
Ma, Nana
Liu, Qingfeng
Zhang, Xingjie
Zhang, Guisheng
author_facet Li, Mengjuan
Li, Jingya
Zhang, Zhiguo
Chen, Liming
Ma, Nana
Liu, Qingfeng
Zhang, Xingjie
Zhang, Guisheng
author_sort Li, Mengjuan
collection PubMed
description A palladium(ii)-catalyzed intramolecular oxidative aza-Wacker-type reaction of vinyl cyclopropanecarboxamides to access a series of conformationally restricted highly substituted aza[3.1.0]bicycles is reported. The transformation proceeded through a typical aza-Wacker reaction mechanism to forge a new C–N bond with oxygen as the terminal oxidant. The desired fused heterocycles were obtained in moderate yields. The process is tolerant of a range of functional aryl groups under mild conditions.
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spelling pubmed-104936472023-09-12 Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles Li, Mengjuan Li, Jingya Zhang, Zhiguo Chen, Liming Ma, Nana Liu, Qingfeng Zhang, Xingjie Zhang, Guisheng RSC Adv Chemistry A palladium(ii)-catalyzed intramolecular oxidative aza-Wacker-type reaction of vinyl cyclopropanecarboxamides to access a series of conformationally restricted highly substituted aza[3.1.0]bicycles is reported. The transformation proceeded through a typical aza-Wacker reaction mechanism to forge a new C–N bond with oxygen as the terminal oxidant. The desired fused heterocycles were obtained in moderate yields. The process is tolerant of a range of functional aryl groups under mild conditions. The Royal Society of Chemistry 2023-09-11 /pmc/articles/PMC10493647/ /pubmed/37701284 http://dx.doi.org/10.1039/d3ra05440c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Li, Mengjuan
Li, Jingya
Zhang, Zhiguo
Chen, Liming
Ma, Nana
Liu, Qingfeng
Zhang, Xingjie
Zhang, Guisheng
Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
title Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
title_full Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
title_fullStr Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
title_full_unstemmed Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
title_short Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
title_sort palladium-catalyzed intramolecular aza-wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10493647/
https://www.ncbi.nlm.nih.gov/pubmed/37701284
http://dx.doi.org/10.1039/d3ra05440c
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