Abstract
Resacetophenone (1) reacts with cinnamyl bromide in the presence of K2CO3 and acetone to give its 4-O-cinnamyl derivative (2); whereas the same reaction in the presence of methanolic methoxide affords 3-C-cinnamyl-(6), 5-C-cinnamyl-(8) and 3,5-di-C-C-cinnamyl- (4) derivatives in the ratio of 36∶1∶15. Reaction of 1 with cinnamyl alcohol in boiling formic acid results in the formation of 8 in the largest amount followed by 6 and a new compound which is a mono-C-cinnamyl flavan (10 or 11). 6 was converted into the corresponding flavan (12), flavene (13) and 4-hydroxycoumarin (14).
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