Premium
Access to Polycyclic Indol(en)ines via Base‐Catalyzed Intramolecular Dearomatizing 3‐Alkenylation of Alkynyl Indoles
Author(s) -
Lu Lin,
Zheng Zuoliang,
Yang Yongjie,
Liu Bo,
Yin Biaolin
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202100164
Subject(s) - chemistry , moiety , intramolecular force , indole test , nucleophile , alkyne , base (topology) , imine , catalysis , medicinal chemistry , nucleophilic addition , stereochemistry , organic chemistry , mathematical analysis , mathematics
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.