STUDIES ON THE SYNTHESIS OF SOME BIOLOGICALLY-ACTIVE FLAVONOID DERIVATIVES .8.

In this study, as a result of the reaction which occurs between epichlorohydrin and 3',4'-dihydroxyflavone, 3',4'-dihydroxy-3-methylflavone and 7,8-dihydroxyflavone derivatives, the ring closure of 1,4-benzodioxane was realized through the A and B rings of the flavones. In the same reaction, two regioisomeric compounds which contain hydroxymethyl group at 2nd or 3rd position (resp.) of dioxan ring were also obtained because of the existence of a non-symmetrical vicinal dihydroxy group on starting compounds. The hydroxymethyl group of these products was converted into the chloromethyl group by using thionyl chloride. In addition, by the alkaline hydrolysis of 2-(2- or 3 ethoxycarbonyl-1,4-benzodioxane-6-yl)-4H-1-benzopyran-4-one, with the 3-methyl derivate of this compound and 7,8-[2-or 3-(ethoxycarbonyl)ethylenedioxy]-2-phenyl-4H-1-benzopyran-4-one, the benzodioxane derivatives which contain carboxyl groups at 2nd or 3rd position were prepared.