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

Autor:	Paul E. Floreancig, Lei Liu, Peter Wipf, Matthew G. LaPorte, Ramy Farid, Nilesh Zaware
Jazyk:	angličtina
Rok vydání:	2011
Předmět:	Tetrahydropyran C-H activation click-chemistry diversity-oriented synthesis Organic chemistry QD241-441
Zdroj:	Molecules, Vol 16, Iss 5, Pp 3648-3662 (2011)
Druh dokumentu:	article
ISSN:	16053648 1420-3049
DOI:	10.3390/molecules16053648
Popis:	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.
Databáze:	Directory of Open Access Journals
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