Base catalyzed dimerization of ω-formyl-2-hydroxyacetophenones

Abstract

Refluxing ω-formyl-2-hydroxyacetophenones 1 in ethanol containing triethylamine as a basic catalyst produced the dimerized product identified as 2-(2-hydroxyaryl)-4H,5H-pyrano[2,3-b]chromen-5-ones 2. Meanwhile, heating ω-formyl-2-hydroxyacetophenones 1 in 2M aqueous sodium hydroxide solution afforded another type of dimeric product identified as 3-[2-(2-hydroxy-5-substituted benzoyl)vinyl]-6-substituted-4H-chromen-4-ones 3. The proposed mechanisms were discussed. The mode of dimerization of ω-formyl-2-hydroxyacetophenones 1 depends on the type of catalyst used and the reaction conditions. Structures of the synthesized compounds were deduced on the basis of their analytical and spectral data.

References

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