Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry

Nilesh Zaware, Matthew G. LaPorte, Ramy Farid, Lei Liu, Peter Wipf, Paul E. Floreancig

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Eighteen (2RS,6RS)-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro- 2Hpyran-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.

Original languageEnglish
Pages (from-to)3648-3662
Number of pages15
JournalMolecules
Volume16
Issue number5
DOIs
StatePublished - May 2011
Externally publishedYes

Keywords

  • C-H activation
  • Click-chemistry
  • Diversity-oriented synthesis
  • Tetrahydropyran

Fingerprint

Dive into the research topics of 'Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry'. Together they form a unique fingerprint.

Cite this