Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions

A highly selective remote C(sp(3))–H acetonation of N-(quinolin-8-yl)amide scaffolds at the C5-position under microwave irradiation has been developed. In the absence of a transition-metal-catalyst, benzoyl peroxide (BPO)-promoted cross-dehydrogenation coupling (CDC) of N-(quinolin-8-yl)amides with...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhou, Chao, Liu, Yunwei, Luo, Qi, Zhang, Yicheng, Zhou, Jingwen, Zhang, Haoyu, Liu, Jie
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/PMC10340454/
https://www.ncbi.nlm.nih.gov/pubmed/37456538
http://dx.doi.org/10.1039/d3ra03651k
_version_ 1785072083503415296
author Zhou, Chao
Liu, Yunwei
Luo, Qi
Zhang, Yicheng
Zhou, Jingwen
Zhang, Haoyu
Liu, Jie
author_facet Zhou, Chao
Liu, Yunwei
Luo, Qi
Zhang, Yicheng
Zhou, Jingwen
Zhang, Haoyu
Liu, Jie
author_sort Zhou, Chao
collection PubMed
description A highly selective remote C(sp(3))–H acetonation of N-(quinolin-8-yl)amide scaffolds at the C5-position under microwave irradiation has been developed. In the absence of a transition-metal-catalyst, benzoyl peroxide (BPO)-promoted cross-dehydrogenation coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile occurred smoothly to generate the corresponding 5-acetonated/acetonitriled N-(quinolin-8-yl)amides in good yields. The transformation is operationally simple, rapid, easily scaled-up to the gram scale, and shows a broad substrate scope.
format Online
Article
Text
id pubmed-10340454
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-103404542023-07-14 Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions Zhou, Chao Liu, Yunwei Luo, Qi Zhang, Yicheng Zhou, Jingwen Zhang, Haoyu Liu, Jie RSC Adv Chemistry A highly selective remote C(sp(3))–H acetonation of N-(quinolin-8-yl)amide scaffolds at the C5-position under microwave irradiation has been developed. In the absence of a transition-metal-catalyst, benzoyl peroxide (BPO)-promoted cross-dehydrogenation coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile occurred smoothly to generate the corresponding 5-acetonated/acetonitriled N-(quinolin-8-yl)amides in good yields. The transformation is operationally simple, rapid, easily scaled-up to the gram scale, and shows a broad substrate scope. The Royal Society of Chemistry 2023-07-13 /pmc/articles/PMC10340454/ /pubmed/37456538 http://dx.doi.org/10.1039/d3ra03651k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Zhou, Chao
Liu, Yunwei
Luo, Qi
Zhang, Yicheng
Zhou, Jingwen
Zhang, Haoyu
Liu, Jie
Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions
title Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions
title_full Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions
title_fullStr Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions
title_full_unstemmed Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions
title_short Microwave-accelerated cross-dehydrogenative-coupling (CDC) of N-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions
title_sort microwave-accelerated cross-dehydrogenative-coupling (cdc) of n-(quinolin-8-yl)amides with acetone/acetonitrile under metal-free conditions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10340454/
https://www.ncbi.nlm.nih.gov/pubmed/37456538
http://dx.doi.org/10.1039/d3ra03651k
work_keys_str_mv AT zhouchao microwaveacceleratedcrossdehydrogenativecouplingcdcofnquinolin8ylamideswithacetoneacetonitrileundermetalfreeconditions
AT liuyunwei microwaveacceleratedcrossdehydrogenativecouplingcdcofnquinolin8ylamideswithacetoneacetonitrileundermetalfreeconditions
AT luoqi microwaveacceleratedcrossdehydrogenativecouplingcdcofnquinolin8ylamideswithacetoneacetonitrileundermetalfreeconditions
AT zhangyicheng microwaveacceleratedcrossdehydrogenativecouplingcdcofnquinolin8ylamideswithacetoneacetonitrileundermetalfreeconditions
AT zhoujingwen microwaveacceleratedcrossdehydrogenativecouplingcdcofnquinolin8ylamideswithacetoneacetonitrileundermetalfreeconditions
AT zhanghaoyu microwaveacceleratedcrossdehydrogenativecouplingcdcofnquinolin8ylamideswithacetoneacetonitrileundermetalfreeconditions
AT liujie microwaveacceleratedcrossdehydrogenativecouplingcdcofnquinolin8ylamideswithacetoneacetonitrileundermetalfreeconditions

Ejemplares similares