Journal
CHEMSUSCHEM
Volume 12, Issue 13, Pages 3043-3048Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201900265
Keywords
aerobic oxidation; alcohols; annulation; o-aminobenzonitriles; quinazolinones
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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.
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