Aerobic Iron(III)-Catalyzed Direct Thiolation of Imidazo[1,2-a]pyridine with Thiols

Ling Qin; Hui-bin Wu; Lidong Weng; Qun Shen; Huoji Chen

doi:10.1055/s-0040-1707517

CC BY-NC-ND 4.0 · SynOpen 2020; 04(02): 17-22
DOI: 10.1055/s-0040-1707517

paper

This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/) (2020) The Author(s)

Aerobic Iron(III)-Catalyzed Direct Thiolation of Imidazo[1,2-a]pyridine with Thiols

Ling Qin

^aDepartment of Pharmaceutics, Nanfang Hospital, Southern Medical University, Guangzhou 510515, P. R. of China

,

Hui-bin Wu

^aDepartment of Pharmaceutics, Nanfang Hospital, Southern Medical University, Guangzhou 510515, P. R. of China

,

Lidong Weng

^bSchool of Traditional Chinese Medicine, Southern Medical University, Shatainan road 1023th, Guangzhou 510515, P. R. of China Email: sq@smu.edu.cn Email: chenhuoji@smu.edu.cn

,

Qun Shen∗

^bSchool of Traditional Chinese Medicine, Southern Medical University, Shatainan road 1023th, Guangzhou 510515, P. R. of China Email: sq@smu.edu.cn Email: chenhuoji@smu.edu.cn

,

Huoji Chen ∗

^bSchool of Traditional Chinese Medicine, Southern Medical University, Shatainan road 1023th, Guangzhou 510515, P. R. of China Email: sq@smu.edu.cn Email: chenhuoji@smu.edu.cn

› Author Affiliations

Abstract

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^§ These authors contributed equally to this work.

Abstract

A novel and efficient iron(III)-catalyzed regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines with thiols under oxygen atmosphere has been developed. The reaction proceeds in moderate to good yields with a broad range of substrates, providing a novel, efficient and green route for accessing synthetically useful C3-sulfenated imidazo-[1,2-a]pyridines. Moreover, the fluoride-containing C3-sulfenated imidazo-[1,2-a]pyridine 3ai exhibited superior anticancer activity and good safety profiles.

Key words

iron-catalyzed - thiolation - imidazo[1,2-a]pyridine - thiols - anticancer activity

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