Bifunctional Urea/Hg(OAc)(2)-Mediated Synthesis of 4-Aryl-6(-)oxycarbonyl-2-pyrones and 2-Pyridones from Dithiomalonate and beta,gamma-Unsaturated alpha-Keto Esters

Bifunctional Urea/Hg(OAc)(2)-Mediated Synthesis of 4-Aryl-6(-)oxycarbonyl-2-pyrones and 2-Pyridones from Dithiomalonate and beta,gamma-Unsaturated alpha-Keto Esters

Disubstituted 2-pyrones and 2-pyridones were obtained by bifunctional urea-catalyzed Michael addition/ lactonization or lactamization followed by a Hg(OAc)(2)- or Hg(OAc)(2)/DBU-mediated hydrolysis/decarboxylation/dehydrogenation process. This one-pot two-stage protocol enabled the rapid synthesis o...

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Veröffentlicht in:Journal of organic chemistry 2021-04, Vol.86 (8), p.6001-6014
Hauptverfasser: Bae, Daeil, Lee, Juyeol, Jin, Hui, Ryu, Do Hyun
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container_end_page 6014
container_issue 8
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container_title Journal of organic chemistry
container_volume 86
creator Bae, Daeil
Lee, Juyeol
Jin, Hui
Ryu, Do Hyun
description Disubstituted 2-pyrones and 2-pyridones were obtained by bifunctional urea-catalyzed Michael addition/ lactonization or lactamization followed by a Hg(OAc)(2)- or Hg(OAc)(2)/DBU-mediated hydrolysis/decarboxylation/dehydrogenation process. This one-pot two-stage protocol enabled the rapid synthesis of 4,6-disubstituted 2-pyrones and 2-pyridones from dithiomalonate and beta,gamma-unsaturated alpha-keto esters in practical yields under mild reaction conditions. Additionally, the obtained 2-pyridones were facilely transformed to 2,4,6-trisubstituted pyridines in excellent yields.
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subjects Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
title Bifunctional Urea/Hg(OAc)(2)-Mediated Synthesis of 4-Aryl-6(-)oxycarbonyl-2-pyrones and 2-Pyridones from Dithiomalonate and beta,gamma-Unsaturated alpha-Keto Esters
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