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I 2 ‐Mediated Iodization/ [3+2] Cycloaddition/Nucleophilic Addition Tandem Reaction: Synthesis of Polyheterocycles Bearing Furoquinoline and Maleimide
Author(s) -
Du Sidong,
Pi Chao,
Wan Ting,
Wu Yangjie,
Cui Xiuling
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801433
Subject(s) - maleimide , chemistry , cycloaddition , quinoline , nucleophilic addition , nucleophile , tandem , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , composite material
An unprecedented metal‐free approach to polyheterocycles bearing furoquinoline and C2‐maleimide‐substituted quinoline has been developed with easily available quinoline N ‐oxides and maleimides via tandem reactions mediated by I 2 , including iodization, [3+2] cycloaddition and nucleophilic addition reactions. I 2 acts as a halogenating agent to promote the subsequent [1,5]‐sigma rearrangement. Two C−O bonds, three C−C bonds and a quaternary carbon center were formed in “one pot” manner.