Reaction of ethyl acetoacetate and 2′-hydroxychalcones: Efficient route to 9-aryl-6H-benzo[c]chromen-6-ones

Abstract

The reaction of ethyl acetoacetate and 2′-hydroxychalcones under atmospheric air to furnish a series of functionalized 6H-benzo[c]chromen-6-ones in moderate yields is reported. The reaction proceeds through trans-esterification, intra-molecular Michael addition, Robinson annulation and oxidative aromatization.

KEY WORDS: 2′-Hydroxychalcones, Ethyl acetoacetate, 6H-Benzo[c]chromen-6-ones, Trans-esterification, Michael addition, Robinson annulation, Oxidative aromatization

Bull. Chem. Soc. Ethiop. 2014, 28(2), 289-294.  

DOI: http://dx.doi.org/10.4314/bcse.v28i2.12