Ultrasound-Promoted and Base-Mediated Regioselective Bromination of Imidazo[1,2-a]pyridines with Pyridinium Tribromide

Hongmei Jiang; Dingyi Guo; Yixin Zhang; Qin-Peng Shen; Shiyun Tang; Junheng You; Yi Huo; Huixian Wang; Qing-Wen Gui

doi:10.1055/s-0040-1707856

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(18): 2713-2720
DOI: 10.1055/s-0040-1707856

paper

Ultrasound-Promoted and Base-Mediated Regioselective Bromination of Imidazo[1,2-a]pyridines with Pyridinium Tribromide

Hongmei Jiang

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China eMail: gqw1216@hunau.edu.cn eMail: gqw1216@163.com

,

Dingyi Guo

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China eMail: gqw1216@hunau.edu.cn eMail: gqw1216@163.com

,

Yixin Zhang

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China eMail: gqw1216@hunau.edu.cn eMail: gqw1216@163.com

,

Qin-Peng Shen

^bChina Yunnan Key Laboratory of Tobacco Chemistry, Research and Development Center, China Tobacco Yunnan Industrial Company, Kunming 650231, P. R. of China

,

Shiyun Tang

^bChina Yunnan Key Laboratory of Tobacco Chemistry, Research and Development Center, China Tobacco Yunnan Industrial Company, Kunming 650231, P. R. of China

,

Junheng You

^bChina Yunnan Key Laboratory of Tobacco Chemistry, Research and Development Center, China Tobacco Yunnan Industrial Company, Kunming 650231, P. R. of China

,

Yi Huo

^cCollege of Nursing, Hunan University of Traditional Chinese Medicine, Changsha 410208, P. R. of China

,

Huixian Wang

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China eMail: gqw1216@hunau.edu.cn eMail: gqw1216@163.com

,

Qing-Wen Gui ∗

^aCollege of Science, Hunan Agricultural University, Changsha 410128, P. R. of China eMail: gqw1216@hunau.edu.cn eMail: gqw1216@163.com

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Abstract

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Abstract

By using pyridinium tribromide as the bromo source, an efficient and practical protocol for the synthesis of C3-brominated imidazo[1,2-a]pyridines through ultrasound-promoted and Na₂CO₃-mediated regioselective bromination of imidazo[1,2-a]pyridines has been developed. This method effectively avoids the use of metal catalysts and harsh reaction conditions, and shows attractive characteristics such as operational simplicity, broad substrate scope with good to excellent yields, ease of scale-up and high energy efficiency.

Key words

bromination - pyridinium tribromide - metal-free synthesis - regioselectivity - imidazopyridines - ultrasonic irradiation - base mediated

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