Regioselective Synthesis and Antibacterial Studies of α,β-Unsaturated Ketone Substituted Cyclohexanols via Tandem Michael Addition-Aldol Addition-Cyclization Sequence under Solvent-Free Conditions

Abstract

A simple and facile strategy was developed involving test tube with glass-rod using a base catalyst for one-pot solid-state reaction between 1,3,5-triphenyl-pentane-1,5-dione (1) and 1,5-diphenyl-penta- 1,4-dien-3-one (2) to obtain novel 1-(5-benzoyl-2-hydroxy-2,4,6-triphenyl-cyclohexyl)-3-phenylpropenone (3) derivatives. The reaction was accomplished in good to excellent yields and the structure of a synthesized compounds was confirmed by IR, 1H NMR and 13C NMR spectral data. In this one-pot transformation, the column chromatography purification was completely avoided. Besides, the method is highly environmentally benign and atom-economical, and the side product of this reaction was only the water molecule. This green process produces significant carbocycles and offers a considerable advantages such as operational simplicity, short reaction time, high yields, and absence of tedious workup. Further, synthesized derivatives was studied against Gram-positive (Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas aeruginosa).