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Molecules 2011, 16(5), 3648-3662; doi:10.3390/molecules16053648

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

1
Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, PA 15260, USA
2
Schrödinger, Inc., 120 West 45th Street, New York, NY 10036, USA
*
Author to whom correspondence should be addressed.
Received: 9 March 2011 / Accepted: 12 April 2011 / Published: 2 May 2011
(This article belongs to the Special Issue Diversity Oriented Synthesis)
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Abstract

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.
Keywords: Tetrahydropyran; C-H activation; click-chemistry; diversity-oriented synthesis Tetrahydropyran; C-H activation; click-chemistry; diversity-oriented synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Zaware, N.; LaPorte, M.G.; Farid, R.; Liu, L.; Wipf, P.; Floreancig, P.E. Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry. Molecules 2011, 16, 3648-3662.

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