Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates

We have developed a procedure for the Michael addition of 4-hydroxycoumarins to vinyl-substituted N-heterocycles. The chemistry is also suitable for thiocoumarins and quinolinones. A mechanism is proposed involving nucleophilic attack at the vinyl-group of the protonated N-heterocycle.

Detalles Bibliográficos
Autores principales: Goka, Benjamin, Klumpp, Douglas A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9900474/
https://www.ncbi.nlm.nih.gov/pubmed/36760300
http://dx.doi.org/10.1039/d3ra00251a
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author Goka, Benjamin
Klumpp, Douglas A.
author_facet Goka, Benjamin
Klumpp, Douglas A.
author_sort Goka, Benjamin
collection PubMed
description We have developed a procedure for the Michael addition of 4-hydroxycoumarins to vinyl-substituted N-heterocycles. The chemistry is also suitable for thiocoumarins and quinolinones. A mechanism is proposed involving nucleophilic attack at the vinyl-group of the protonated N-heterocycle.
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spelling pubmed-99004742023-02-08 Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates Goka, Benjamin Klumpp, Douglas A. RSC Adv Chemistry We have developed a procedure for the Michael addition of 4-hydroxycoumarins to vinyl-substituted N-heterocycles. The chemistry is also suitable for thiocoumarins and quinolinones. A mechanism is proposed involving nucleophilic attack at the vinyl-group of the protonated N-heterocycle. The Royal Society of Chemistry 2023-02-06 /pmc/articles/PMC9900474/ /pubmed/36760300 http://dx.doi.org/10.1039/d3ra00251a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Goka, Benjamin
Klumpp, Douglas A.
Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates
title Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates
title_full Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates
title_fullStr Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates
title_full_unstemmed Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates
title_short Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates
title_sort synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted n-heterocycles with 4-hydroxycoumarin and related substrates
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9900474/
https://www.ncbi.nlm.nih.gov/pubmed/36760300
http://dx.doi.org/10.1039/d3ra00251a
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AT klumppdouglasa synthesisofwarfarinanalogsconjugateadditionreactionsofalkenylsubstitutednheterocycleswith4hydroxycoumarinandrelatedsubstrates

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