One-Pot Synthesis of 4-Quinolone via Iron-Catalyzed Oxidative Coupling of Alcohol and Methyl Arene
Seok Beom Lee, Yoonkyung Jang, Jiwon Ahn, Simin Chun, Dong‐Chan Oh, Suckchang Hong
Abstract
Herein, we describe the iron(III)-catalyzed oxidative coupling of alcohol/methyl arene with 2-amino phenyl ketone to synthesize 4-quinolone. Alcohols and methyl arenes are oxidized to the aldehyde in the presence of an iron catalyst and di-tert-butyl peroxide, followed by a tandem process, condensation with amine/Mannich-type cyclization/oxidation, to complete the 4-quinolone ring. This method tolerates various kinds of functional groups and provides a direct approach to the synthesis of 4-quinolones from less functionalized substrates.
Topics & Concepts
ChemistryCatalysisAlcoholOxidative coupling of methaneAldehydeKetoneAmine gas treatingQuinoloneOxidative phosphorylationMethyl KetoneCombinatorial chemistryOrganic chemistryMedicinal chemistryBiochemistryAntibioticsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthetic Organic Chemistry Methods