Gold(I)-Catalyzed Pathway-Switchable Syntheses of Azocine[4,5- b ]indole and (1 H -indol-3-yl)-Azepino[4,5- b ]indole Derivatives

作者：Jiaji Li, Zhibin Zhao, Ziqiang Xu, Qing Jiang, Sen Zhang, Lianjie Zhang, Bin Lin, Lu Yang, Maosheng Cheng, Yongxiang Liu · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.5c01296 · 被引用次数：4 · 研究领域：Catalytic Alkyne Reactions、Catalytic C–H Functionalization Methods、Oxidative Organic Chemistry Reactions

A pathway-switchable gold(I)-catalyzed N -propargyl tryptamine cycloisomerization strategy was developed and successfully used for the syntheses of azocine[4,5- b ]indole and (1 H -indol-3-yl)-azepino[4,5- b ]indole derivatives. The optimal reaction conditions for the two pathways were determined through detailed studies, and the scope of this pathway-switchable approach was explored using a series of N -propargyl tryptamine substrates. A gold(I)-catalyzed 8- endo -dig or 7- exo -dig cycloisomerization mechanism regulated by substituents and nucleophiles was proposed.