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Metal‐free Deoxygenative 2‐Amidation of Quinoline N ‐oxides with Nitriles via a Radical Activation Pathway
Author(s) -
Xie LongYong,
Peng Sha,
Liu Fang,
Yi JinYu,
Wang Ming,
Tang Zilong,
Xu Xinhua,
He WeiMin
Publication year - 2018
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.201800918
Subject(s) - chemistry , regioselectivity , reagent , amide , quinoline , electrophile , combinatorial chemistry , radical , surface modification , metal , organic chemistry , photochemistry , catalysis
A metal‐, base‐ and reductant‐free approach for the efficient synthesis of various N ‐acylated 2‐aminoquinolines was reported. In this work, readily available nitriles are used as the amide source, and methyl carbazate as both the radical activating reagent and oxygen source. This is the first report on the ester‐radical‐activated highly regioselective addition of nitriles to quinolone N ‐oxides. This procedure is expected to complement the current methods for functionalization of N ‐oxides via an electrophilic activation mechanism.