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

Molecules

Nilesh Zaware¹  Matthew G. LaPorte¹  Ramy Farid¹  Lei Liu¹  Peter Wipf¹ 

[1] ¹Department of Chemistry and Center for Chemical Methodologies & Library Development, University of Pittsburgh, Pittsburgh, PA 15260, USA ²Schrödinger, Inc., 120 West 45th Street, New York, NY 10036, USA

关键词: Tetrahydropyran;    C-H activation;    click-chemistry;    diversity-oriented synthesis;   

DOI  :  10.3390/molecules16053648

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.