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CC BY-NC-ND 4.0 · SynOpen 2020; 04(02): 17-22
DOI: 10.1055/s-0040-1707517
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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
a   Department of Pharmaceutics, Nanfang Hospital, Southern Medical University, Guangzhou 510515, P. R. of China
,
Hui-bin Wu
a   Department of Pharmaceutics, Nanfang Hospital, Southern Medical University, Guangzhou 510515, P. R. of China
,
Lidong Weng
b   School 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∗
b   School 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  ∗
b   School 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 AffiliationsFunding was provided by the Natural Science Foundation of Guangdong Province (2017A030310021), the Science and Technology Program of Guangdong Province (2017A050506027, 2017B090912005) and the Science and Technology Program of Guangzhou (201807010053).
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Publication History

Received: 10 March 2020

Accepted after revision: 31 March 2020

Publication Date:
21 April 2020 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690903.
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