Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry

Eighteen (2RS,6RS)-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro-2H-pyran-4(3H)ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactio...

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Autores principales: Zaware, Nilesh, LaPorte, Matthew G., Farid, Ramy, Liu, Lei, Wipf, Peter, Floreancig, Paul E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263335/
https://www.ncbi.nlm.nih.gov/pubmed/21540794
http://dx.doi.org/10.3390/molecules16053648
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author Zaware, Nilesh
LaPorte, Matthew G.
Farid, Ramy
Liu, Lei
Wipf, Peter
Floreancig, Paul E.
author_facet Zaware, Nilesh
LaPorte, Matthew G.
Farid, Ramy
Liu, Lei
Wipf, Peter
Floreancig, Paul E.
author_sort Zaware, Nilesh
collection PubMed
description Eighteen (2RS,6RS)-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro-2H-pyran-4(3H)ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactions. Examples of a linked benzotriazole and pyrazole motif were also prepared. To complement the structural diversity, the alcohol substrates were obtained from stereoselective reductions of the tetrahydropyrone. This library provides rapid access to structurally diverse non-natural compounds to be screened against a variety of biological targets.
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spelling pubmed-62633352018-12-10 Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry Zaware, Nilesh LaPorte, Matthew G. Farid, Ramy Liu, Lei Wipf, Peter Floreancig, Paul E. Molecules Article Eighteen (2RS,6RS)-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro-2H-pyran-4(3H)ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactions. Examples of a linked benzotriazole and pyrazole motif were also prepared. To complement the structural diversity, the alcohol substrates were obtained from stereoselective reductions of the tetrahydropyrone. This library provides rapid access to structurally diverse non-natural compounds to be screened against a variety of biological targets. MDPI 2011-05-02 /pmc/articles/PMC6263335/ /pubmed/21540794 http://dx.doi.org/10.3390/molecules16053648 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Zaware, Nilesh
LaPorte, Matthew G.
Farid, Ramy
Liu, Lei
Wipf, Peter
Floreancig, Paul E.
Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry
title Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry
title_full Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry
title_fullStr Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry
title_full_unstemmed Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry
title_short Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry
title_sort diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263335/
https://www.ncbi.nlm.nih.gov/pubmed/21540794
http://dx.doi.org/10.3390/molecules16053648
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