Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines

N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C–C bond cleavage promoted by I(2) and TBHP and the reaction conditions were mild and...

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Autores principales: Liu, Yanpeng, Lu, Lixue, Zhou, Haipin, Xu, Feijie, Ma, Cong, Huang, Zhangjian, Xu, Jinyi, Xu, Shengtao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073897/
https://www.ncbi.nlm.nih.gov/pubmed/35529989
http://dx.doi.org/10.1039/c9ra06724h
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author Liu, Yanpeng
Lu, Lixue
Zhou, Haipin
Xu, Feijie
Ma, Cong
Huang, Zhangjian
Xu, Jinyi
Xu, Shengtao
author_facet Liu, Yanpeng
Lu, Lixue
Zhou, Haipin
Xu, Feijie
Ma, Cong
Huang, Zhangjian
Xu, Jinyi
Xu, Shengtao
author_sort Liu, Yanpeng
collection PubMed
description N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C–C bond cleavage promoted by I(2) and TBHP and the reaction conditions were mild and metal-free. Whereas 3-bromoimidazopyridines were obtained in ethyl acetate via one-pot tandem cyclization/bromination when only TBHP was added, the cyclization to form imidazopyridines was promoted by the further bromination, no base was needed, and the versatile 3-bromoimidazopyridines could be further transferred to other skeletons.
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spelling pubmed-90738972022-05-06 Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines Liu, Yanpeng Lu, Lixue Zhou, Haipin Xu, Feijie Ma, Cong Huang, Zhangjian Xu, Jinyi Xu, Shengtao RSC Adv Chemistry N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C–C bond cleavage promoted by I(2) and TBHP and the reaction conditions were mild and metal-free. Whereas 3-bromoimidazopyridines were obtained in ethyl acetate via one-pot tandem cyclization/bromination when only TBHP was added, the cyclization to form imidazopyridines was promoted by the further bromination, no base was needed, and the versatile 3-bromoimidazopyridines could be further transferred to other skeletons. The Royal Society of Chemistry 2019-10-28 /pmc/articles/PMC9073897/ /pubmed/35529989 http://dx.doi.org/10.1039/c9ra06724h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Liu, Yanpeng
Lu, Lixue
Zhou, Haipin
Xu, Feijie
Ma, Cong
Huang, Zhangjian
Xu, Jinyi
Xu, Shengtao
Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
title Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
title_full Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
title_fullStr Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
title_full_unstemmed Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
title_short Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
title_sort chemodivergent synthesis of n-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073897/
https://www.ncbi.nlm.nih.gov/pubmed/35529989
http://dx.doi.org/10.1039/c9ra06724h
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