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 language | English |
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Pages (from-to) | 3648-3662 |
Number of pages | 15 |
Journal | Molecules |
Volume | 16 |
Issue number | 5 |
DOIs | |
State | Published - May 2011 |
Externally published | Yes |
Keywords
- C-H activation
- Click-chemistry
- Diversity-oriented synthesis
- Tetrahydropyran