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由α-溴代酮和2-氨基吡啶进行化学发散合成-(吡啶-2-基)酰胺和3-溴咪唑并[1,2 -]吡啶。

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

作者信息

Liu Yanpeng, Lu Lixue, Zhou Haipin, Xu Feijie, Ma Cong, Huang Zhangjian, Xu Jinyi, Xu Shengtao

机构信息

State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University 24 Tong Jia Xiang Nanjing 210009 China

Department of Chemistry, City University of Hong Kong 83 Tat Chee Avenue Hong Kong SAR P. R. China.

出版信息

RSC Adv. 2019 Oct 28;9(59):34671-34676. doi: 10.1039/c9ra06724h. eCollection 2019 Oct 23.

DOI:10.1039/c9ra06724h
PMID:35529989
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9073897/
Abstract

-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. -(Pyridin-2-yl)amides were formed in toluene C-C bond cleavage promoted by I and TBHP and the reaction conditions were mild and metal-free. Whereas 3-bromoimidazopyridines were obtained in ethyl acetate 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.

摘要

-(吡啶-2-基)酰胺和3-溴咪唑并[1,2 -]吡啶分别在不同反应条件下由α-溴代酮和2-氨基吡啶合成。-(吡啶-2-基)酰胺在甲苯中由碘和叔丁基过氧化氢促进碳-碳键断裂形成,反应条件温和且无金属。而3-溴咪唑并吡啶在乙酸乙酯中通过一锅串联环化/溴化反应得到,当仅加入叔丁基过氧化氢时,进一步的溴化促进了形成咪唑并吡啶的环化反应,无需碱,并且通用的3-溴咪唑并吡啶可以进一步转化为其他骨架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/c970a4e45c95/c9ra06724h-s6.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/391cbf39275e/c9ra06724h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/28c68e848382/c9ra06724h-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/c970a4e45c95/c9ra06724h-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/0bd0069f9c29/c9ra06724h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/e65c3978c3c4/c9ra06724h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/57229a2f8d19/c9ra06724h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/9178b98f1fb2/c9ra06724h-s3.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/28c68e848382/c9ra06724h-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24f6/9073897/c970a4e45c95/c9ra06724h-s6.jpg

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