Premium
Facile Construction of Quinoline‐2‐carboxylate Esters through Aerobic Oxidation of Alkyl 4‐Anilinocrotonates Induced by a Radical Cation Salt
Author(s) -
Jia Xiaodong,
Li Pengfei,
Shao Yu,
Yuan Yu,
Hou Wentao,
Liu Xiaofei,
Zhang Xuewen,
Ji Honghe
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700560
Subject(s) - quinoline , chemistry , salt (chemistry) , alkyl , carboxylate , catalysis , domino , organic chemistry , combinatorial chemistry
A facile construction of quinoline‐2‐carboxylate esters through an aerobic oxidation of alkyl 4‐anilinocrotonates is described. In the presence of dioxygen, sp 3 C−H bonds in 4‐anilinocrotonates can easily be oxidized by using a catalytic amount of a radical cation salt, providing a radical intermediate. After further oxidation and domino cyclization, the desired quinoline derivatives were afforded in high yields. This reaction provides a new way to construct the pharmaceutically relevant quinoline skeleton, avoiding harsh reaction conditions and tedious starting material synthesis.