Electrophilic Sulfenylation/Cyclization of N‐Aryl and N‐Benzyl Propynamides: Synthesis of Sulfenyl Quinolinones and 3H‐Benzo[c]azepin‐3‐ones

Quinolinones and benzo[c]azepinones are important cores in biologically active molecules. We report the cyclization of N‐substituted propynamides, initiated by readily available electrophilic sulfenylating agent, enabling the synthesis of quinolinones and benzo[c]azepinones in exceedingly simple con...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2023-08, Vol.12 (8), p.n/a
Main Authors: Yang, Ping, Tang, Meizhong, Liu, Yankui, Zhang, Weijun, Wang, Ye‐Xin, Wang, Jia, Xie, Lan‐Gui
Format: Article
Language:English
Subjects:
benzo[c]azepinone
cyclization
dimethyl(methylthio)sulfonium trifluoromethanesulfonate
quinolinone
sulfenylation
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Summary:Quinolinones and benzo[c]azepinones are important cores in biologically active molecules. We report the cyclization of N‐substituted propynamides, initiated by readily available electrophilic sulfenylating agent, enabling the synthesis of quinolinones and benzo[c]azepinones in exceedingly simple conditions. The approach shows excellent generality to the substrates and tolerability of functional groups. The anti‐inflammatory effect of the newly synthesized 3‐sulfenyl quinolinone and the 4‐sulfenyl benzo[c]azepinone products are tested, and two compounds are confirmed to have inhibitive effect on TNF‐α expression. A sulfenylation/cyclization reaction of N‐substituted propynamides has been developed with dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTSM) as the initiator, providing the modular synthesis of 3‐sulfenyl quinolinones and 4‐sulfenyl benzo[c]azepinones.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300349