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Synthesis of substituted quinolines via B(C 6 F 5 ) 3 ‐catalyzed aniline‐aldehyde‐pyruvate oxidative annulation
Author(s) -
Ling Fei,
Chen Jiachen,
Xie Zhen,
Hou Huacui,
Pan Zhentao,
Feng Cong,
Shen Haiwei,
Zhong Weihui
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3730
Subject(s) - chemistry , aniline , aldehyde , quinoline , annulation , yield (engineering) , catalysis , combinatorial chemistry , organic chemistry , materials science , metallurgy
A metal‐free method to construct quinoline derivatives via B(C 6 F 5 ) 3 ‐catalyzed cyclization of anilines with aldehyde derivatives and pyruvates is described. This three‐component cascade reaction provides an efficient approach for the easy access to various substituted quinoline‐4‐carboxylic esters with 71% to 92% yield. The utility of this methodology was further demonstrated by gram‐scale formal synthesis of the antimalarial drug DDD107498.