A study of the sequential michael addition-ring closure reaction of ethyl acetoacetate with chalcone: Influence of quaternary ammonium cations as phase transfer catalysts

Abstract

The Michael addition of ethyl acetoacetate 1 to chalcone 2 under Solid/Liquid Phase Transfer Catalysis (SL-PTC), solvent free, afforded Michael adduct 3 and an annulated compound 4 in good yield. The cyclic compound 4 was obtained in the majority via an annulation process of the Michael adduct 3. The proportion of 4 in the ratio of 3/4 was dependant on the structure of the quaternary ammonium cation. The results were interpreted on the basis of the organophilicity and accessibility of the catalysts as well as by invoking a 6-membered ring transition state for the formation of 4 due to the chelation level with Q+. ©2005 Sociedade Brasileira de Química.