A DBU-Catalyzed Rearrangement of 4-Hydroxy-3-Coumarinylchalcones to δ-Valerolactone-Fused Coumarins

Abstract

The reaction of 4-hydroxy-3-coumarinylchalcone with acetylacetone in the presence of base was expected to result in Michael adduct. During this reaction in the presence of catalytic amount of DBU a rearrangement led to δ-valerolactone [3,4]-fused coumarin. The outcome of this rearrangement was almost the same in the presence or absence of active methylene compounds. Preliminary screening tests of the synthesized derivatives for LOX (lipoxygenase) inhibition activity and anticancer activity were performed.

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