Next Article in Journal
Next Article in Special Issue
Previous Article in Journal
Previous Article in Special Issue
Molecules 2011, 16(5), 3648-3662; doi:10.3390/molecules16053648
Article

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

1, 1, 2, 1, 1 and 1,*
Received: 9 March 2011; Accepted: 12 April 2011 / Published: 2 May 2011
(This article belongs to the Special Issue Diversity Oriented Synthesis)
Download PDF [315 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.

AMA Style

Zaware N, LaPorte MG, Farid R, Liu L, Wipf P, Floreancig PE. Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry. Molecules. 2011; 16(5):3648-3662.

Chicago/Turabian Style

Zaware, Nilesh; LaPorte, Matthew G.; Farid, Ramy; Liu, Lei; Wipf, Peter; Floreancig, Paul E. 2011. "Diversity-Oriented Synthesis of a Library of Substituted Tetrahydropyrones Using Oxidative Carbon-Hydrogen Bond Activation and Click Chemistry." Molecules 16, no. 5: 3648-3662.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert