BiCl 3 ‐Mediated Tandem Cyclization of Tryptamine‐Derived Ynamide: Concise Synthesis of Pentacyclic Spiroindolines and Tricyclic Indole Derivatives

作者：Xiaotong Lin, Cheng Zhao, Da‐Ru Wang, Guang‐Cheng Wu, Guo‐Shu Chen, Shu‐Jie Chen, Hai Ren, Dongsheng Deng, Yi‐Bing Xu, Xiao‐Wei Hu, Yun‐Lin Liu · 发表于：Advanced Synthesis & Catalysis · 年份：2021 · DOI：10.1002/adsc.202101232 · 被引用次数：13 · 研究领域：Catalytic Alkyne Reactions、Cyclopropane Reaction Mechanisms、Catalytic C–H Functionalization Methods

Abstract Catalytic tandem cyclization of ynamides has attracted considerable interest in organic synthesis because of its atom economy in the rapid formation of polycyclic compounds. However, examples on the construction of pentacyclic spiroindolines are quite scarce. Herein, we described a BiCl 3 ‐mediated tandem cyclization reaction of tryptamine‐ynamides, which led to the formation of appealing pentacyclic spiroindoline scaffolds in moderate to excellent yields. In addition, such a reaction can lead to the divergent synthesis of tricyclic indole derivatives with moderate yields by engineering substrate structures. The synthetic utility of this methodology has also been demonstrated by further interesting transformations. magnified image