Palladium-Catalyzed N -Nucleophilic Ring-Opening Reaction of Spiro-vinylcyclopropyl Oxindoles and Synthetic Conversion

作者：Xing-Tong Li, Ming‐Xing Lan, Xia Yu, Xue‐Qing Mou, Mei Bai, Yong‐Zheng Chen, Bao‐Dong Cui · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.5c02258 · 被引用次数：3 · 研究领域：Cyclopropane Reaction Mechanisms、Catalytic C–H Functionalization Methods、Catalytic Alkyne Reactions

-nucleophilic ring-opening reaction of spiro-vinylcyclopropyl oxindoles introducing an azido or a substituted amino group into the C3 position has been developed. Using palladium (0) as the catalyst, the racemic spiro-vinylcyclopropyl oxindoles can not only be converted to their chiral diastereoisomers via a stereoisomerization process but also generate a series of azido-substituted oxindole derivatives through the nucleophilic azide addition or be transformed to tertiary amine-substituted oxindoles through a simple ring-opening process. Notably, the azide products can serve as an important synthetic intermediate to successfully convert to other 3-substituted oxindole derivatives and the spiro[furan-3,3'-oxindoles], which exhibit good antitumor activity in vitro, thus demonstrating their potential applications in medicinal chemistry.