A New Reaction Mode of 3-Halooxindoles: Acting as C-C-O Three-Atom Components for (3+3) Cycloaddition to Access Indolenine-Fused 2 H -1,4-Oxathiines

Herein, we report an unprecedented implementation of 3-halooxindoles as C-C-O three-atom components for (3+3) cycloaddition with pyridinium 1,4-zwitterionic thiolates, affording structurally diverse indolenine-fused 2 -1,4-oxathiines in moderate to high yields. A combined experimental and computatio...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (51), p.9191-9196
Main Authors: Sun, Ting-Jia, Peng, Xue-Song, Sun, Wei, Zhang, Yan-Ping, Ma, Xiao-Min, Zhao, Jian-Qiang, Wang, Zhen-Hua, You, Yong, Zhou, Ming-Qiang, Yin, Jun-Qing, Yuan, Wei-Cheng
Format: Article
Language:English
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Summary:Herein, we report an unprecedented implementation of 3-halooxindoles as C-C-O three-atom components for (3+3) cycloaddition with pyridinium 1,4-zwitterionic thiolates, affording structurally diverse indolenine-fused 2 -1,4-oxathiines in moderate to high yields. A combined experimental and computational mechanistic study suggests that the reaction proceeds through addition of a S conjugate to the -azaxylylene intermediate, followed by O-Michael addition and a sequential retro-Michael addition/pyridine extrusion pathway.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03745