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Synthesis of Iodine‐Substituted Quinolines, Quinolinium Salts, and Isoquinolinium Salts via a Three‐Component Tandem Reaction of Aryl Azides, Propargylic Alcohols, and Iodine
Author(s) -
Wu Yunjun,
Shao Min,
Feng Zhijun,
Gu Xiaoxia,
Hong Yi,
Cui Qiaoyu,
Ren Lianbing,
Wang Shaoyin
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600503
Subject(s) - chemistry , aryl , cascade reaction , isoquinoline , iodine , electrophile , tandem , salt (chemistry) , organic chemistry , combinatorial chemistry , medicinal chemistry , alkyl , catalysis , materials science , composite material
An efficient three‐component tandem reaction of aryl azides, propargylic alcohols, and iodine has been developed. The products of the reaction hinge on the type of the propargylic alcohols: for tertiary alcohols, the reaction proceeded via a cascade Friedel–Crafts‐type reaction/electrophilic cyclization/1,2‐aryl migratory shift sequence to provide 3‐iodoquinolinium salt products, while in the case of secondary alcohols, 3‐iodoquinoline products could be obtained. For aryl azides with certain substituents, this method gave novel isoquinoline skeletons.