Claisen-Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives with different substituents in H2O/EtOH

A simple, green, and direct three-component condensation of acetophenone, aromatic aldehydes with 3-oxo-N-phenylbutanamide (acetoacetanilide) to generate some novel (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives was carried out over K2CO3 (10mol%) with high efficiency in water/ethanol as green solvent at room temperature. This protocol proceeded via Claisen-Schmidt condensation and Michael addition. The present methodology offers several advantages, such as short reaction time, high yield, more readily available and inexpensive materials, more environmentally friendly, no need for column chromatography, simple work-up procedure, and the absence of volatile and hazardous organic solvents.