6515-31-7Relevant 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.
A convenient and general synthesis of trans-3-hydroxyflavanones from chalcones by dimethyldioxirane epoxidation and subsequent base-catalyzed cyclization
Patonay,Toth,Adam
, p. 5055 - 5058 (2007/10/02)
2'-Hydroxychalcone epoxides were found to give trans-3-hydroxyflavanone and 2-(α-hydroxybenzyl)-3-coumaranone under basic conditions. Epoxidation of 2'-hydroxychalcones with dimethyldioxirane followed by treatment of tetrabutylammonium hydroxide provides a convenient and general method for the synthesis of trans-3-hydroxyflavanones.
Heterocycles. XX. Reactions of 2''-Methoxymethoxychalcone Epoxides under Acidic Conditions
Takahashi, Hiroshi,Kubota, Yumiko,Fang, Lin,Li, Shaoshun,Onda, Masayuki
, p. 4597 - 4604 (2007/10/02)
The effect of substituents on the formation of products in the reactions of 2''-methoxymethoxychalcone epoxides under acidic conditions has been examined.Regardless of the 6''-substituent, the presence of a 4'-hydroxyl group results in the exlusive format