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. 2011 Aug 19;13(16):4228-31.
doi: 10.1021/ol2015658. Epub 2011 Jul 13.

Gold catalyzed cyclization of alkyne-tethered dihydropyrimidones

Lauren E Brown  1 , Peng Dai, John A Porco Jr, Scott E Schaus
Affiliations

Gold catalyzed cyclization of alkyne-tethered dihydropyrimidones

Lauren E Brown et al. Org Lett. .

Abstract

Dihydropyrimidones are an important class of biologically active heterocycles accessible from the multicomponent Biginelli condensation. Further manipulation of the dihydropyrimidone skeleton gives access to unique heterocycles. Presented herein is a Au-catalyzed cyclization of alkyne-tethered dihydropyrimidones to yield pyridopyrimidones.

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Figures

Figure 1
Figure 1
Screened catalysts and conditions
Figure 2
Figure 2
Proposed mechanism for pyridopyrimidone formation
Figure 3
Figure 3
Plot of the steady-state intial rate of product formation vs auric acid concentration cubed for the conversion of 14 to 27 (ClCH2CH2Cl, 25 °C)
Figure 4
Figure 4
Proposed bimetallic Au(III) carbonyl activation
Scheme 1
Scheme 1
Synthesis of additional substrates for reaction screen
Scheme 2
Scheme 2
Deuterium labeling studies
See this image and copyright information in PMC

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