Electrochemically enabled synthesis of sulfide imidazopyridinesviaa radical cyclization cascade

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 pyridinesviaa radical...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 19; pp. 6334 - 6339
Main Authors Zhong, Ping-Fu, Lin, Hong-Min, Wang, Lin-Wei, Mo, Zu-Yu, Meng, Xiu-Jin, Tang, Hai-Tao, Pan, Ying-Ming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.10.2020
Subjects
Chemistry
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Physical Sciences
Science & Technology
Science & Technology - Other Topics
DESIGN
VINYL AZIDES
PYRIDINE
TRIFLUOROMETHYLATION
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Summary: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 pyridinesviaa 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.
ISSN:1463-9262
1463-9270
DOI:10.1039/d0gc02125c