Issue 19, 2020
From the journal:

Green Chemistry

Electrochemically enabled synthesis of sulfide imidazopyridines via a radical cyclization cascade†

Ping-Fu Zhong,a   Hong-Min Lin,a   Lin-Wei Wang,a   Zu-Yu Mo,a   Xiu-Jin Meng,a   Hai-Tao Tang ORCID logo *a  and  Ying-Ming Pan ORCID logo *a  

* Corresponding authors

a State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China
E-mail: panym@mailbox.gxnu.edu.cn, httang@gxnu.edu.cn

Abstract

Owing to the inert nature of the pyridine ring and high activity of iminyl radicals, the reaction between pyridine and iminyl radicals remains a significant challenge. In this paper, we report the synthesis of sulfide imidazo[1,2-a]pyridines from vinyl azides, thiophenols, and pyridines via a radical [3 + 2] cycloaddition. Promoting inert pyridine and highly active iminyl radicals to participate in this intermolecular cycloaddition process is the striking feature of this protocol. The excellent antitumor activity of the prepared sulfide imidazopyridine scaffold demonstrated the synthetic utility of the developed synthetic protocol.

Graphical abstract: Electrochemically enabled synthesis of sulfide imidazopyridines via a radical cyclization cascade

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Article information

DOI
https://doi.org/10.1039/D0GC02125C
Article type
Communication
Submitted
22 Jun 2020
Accepted
25 Aug 2020
First published
26 Aug 2020

Green Chem., 2020,22, 6334-6339

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Electrochemically enabled synthesis of sulfide imidazopyridines via a radical cyclization cascade

P. Zhong, H. Lin, L. Wang, Z. Mo, X. Meng, H. Tang and Y. Pan, Green Chem., 2020, 22, 6334 DOI: 10.1039/D0GC02125C

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