The synthesis of α,β-epoxy-2'-hydroxychalcones (3-aryl-2,3-epoxy-1-(2-hydroxyaryl)propanones) 2 by direct epoxidation of (E)-2'-hydroxychalcones [(E)-3-aryl-1-(2-hydroxyaryl)propenone] 1 with dimethyldioxirane at subambient temperatures is reported. These acid- and base-sensitive epoxides, which have been hitherto difficult to prepare, were isolated in excellent yields and were completely characterized by spectral and microanalytical data. The now readily available 2'-hydroxy substituted chalcone oxides may serve as convenient precursors to flavonoid-type natural products.
ASJC Scopus subject areas
- Organic Chemistry