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Efficient Synthesis of Quinazolinones by Transition‐Metal‐Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o ‐Aminoarylnitriles
Author(s) -
Wang Qi,
Lv Miao,
Liu Jianping,
Li Yang,
Xu Qing,
Zhang Xu,
Cao Hongen
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201900265
Subject(s) - annulation , transition metal , chemistry , cascade , combinatorial chemistry , cascade reaction , catalysis , organic chemistry , chromatography
A mild and atom‐economic method was developed for direct and efficient synthesis of quinazolinones through a transition‐metal‐free aerobic oxidative cascade annulation reaction of widely available o ‐aminoarylnitriles and alcohols. Air could be employed as an effective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the “cesium effect”, the water‐soluble base CsOH was found to be crucial in all key steps of the reaction mechanism. Because a wide range of substrates can be used to prepare substituted quinazolinones without contamination by transition‐metal residues, this method may be of interest for application in pharmaceutical synthesis. Possible reaction paths were also proposed according to control reactions.