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One-Pot Selective Saturation and Functionalization of Heteroaromatics Leading to Dihydropyridines and Dihydroquinolines
journal contribution
posted on 2020-03-18, 14:41 authored by Dong Wang, Yuanyang Jiang, Linru Dong, Gaoyu Li, Baoying Sun, Laurent Désaubry, Peng YuA one-pot regioselective two C–C-bond-forming
dearomatization
of pyridines and quinolines is disclosed. Two 3,4-betaines are identified
for the first time as very useful organic synthons in heterocyclic
chemistry. Furthermore, the chemical reactivity of the prepared trifluoromethyl
ketones, a new type of push–pull enones, has been explored
to develop straightforward methods for their functionalization. This
protocol represents a breakthrough in the dearomatization of heteroaromatics
as both the selective saturation and functionalization of heteroaromatics
are achieved in high efficiency by the attachment of two substituents,
including the valuable trifluoromethyl ketone group.
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heteroaromaticsynthonbreakthroughFunctionalizationSaturationsaturationattachmenttypemethodchemical reactivitysubstituenttrifluoromethyl ketone groupfunctionalizationpyridinetrifluoromethyl ketonesOne-Potenoneheterocyclic chemistryDihydroquinolineHeteroaromaticefficiencydearomatizationbetaineDihydropyridineone-pot regioselectivequinoline
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