10173-78-1Relevant articles and documents
Flavonoid epoxides. Part 20. Some unusual reactions of dimethyldioxirane (DMD) with flavonoid compounds
Burke, Anthony J.,O'Sullivan, W. Ivo
, p. 8491 - 8500 (2007/10/03)
Dimethyldioxirane (DMD), generally as a solution in acetone, has proved itself to be an excellent epoxidising agent. It was observed that either the 2'-hydroxychalcone epoxide or the tans-2,3-dihydroflavonol could be obtained depending on the pH of the reaction mixture and the type of β-arene ring present in the substrate. Using this methodology trans-2,3-dihydroflavonols can be synthesised in far better yields than by the most commonly used method for their synthesis, that of the Algar-Flynn-Oyamada reaction. Treatment of both flavonol 14 and the novel isoaurone 21 with DMD gave unusual products instead of the expected epoxides, but nonetheless, an epoxide was assumed to have formed during the reaction.
Flavonoid Epoxides. Part 16. Synthesis and Base-catalysed Rearrangement of Aurone Epoxides
Brady, Brian A.,Geoghegan, Michael,McMurtey, Kenneth D.,O'Sullian, Ivo W.
, p. 119 - 123 (2007/10/02)
A number of new aurone epoxides have been synthesised by improved method of alkaline hydrogen peroxide epoxidation of aurones.Flavonols were the main products when the reaction period was prolonged.Aurone epoxides on reaction with base rearranged to flavonols and to aroylcoumaran-3-ones.Aurone epoxides may also be synthesised by the Darzens condensation.