Access to Polycyclic Indol(en)ines via Base-Catalyzed Intramolecular Dearomatizing 3-Alkenylation of Alkynyl Indoles

作者：Lu, Lin; Zheng, Zuoliang; Yang, Yongjie; Liu, Bo^*; Yin, Biaolin^*

来源：Chinese Journal of Chemistry, 2021, 39(8): 2207-2212.

DOI：10.1002/cjoc.202100164

• Dearomatization
• Domino reaction
• Alkynyl indole
• Synthetic method
• Cyclization

Main observation and conclusion Polycyclic indolines and indolenines were synthesized via base-catalyzed intramolecular dearomatizing 3-alkenylation reactions of alkynyl indoles 1 at room temperature. The base enhanced the nucleophilicity of the carbon at the 3-position of the indole moiety, facilitating an exclusive 5-exo-dig cyclization reaction with the alkyne to form spiroindolenines 2. The imine functionality of 2 could undergo in situ nucleophilic addition to form spiroindolines 3 when R was a carbamoyl group or reduction to form spiroindolines 4 when R was H.

• 单位
  广州中医药大学