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Vol. 34 No. 10 (2022): Vol 34 Issue 10, 2022

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

https://doi.org/10.14233/ajchem.2022.23907
Tevaraj Suriyakala
Department of Chemistry, Cardamom Planters’ Association College, Bodinayakanur-625513, India
Alagiri Chinnaraj
Department of Chemistry, Cardamom Planters’ Association College, Bodinayakanur-625513, India
Velmurugan Senthilkumar
Department of Chemistry, Cardamom Planters’ Association College, Bodinayakanur-625513, India
Mohamedsulaiman Kamal Nasar
Department of Chemistry, Hajee Karutha Rowther Howdia College, Uthamapalayam-625533, India
Gurusamy Ravindran
Department of Chemistry, Cardamom Planters’ Association College, Bodinayakanur-625513, India

Corresponding Author(s) : Gurusamy Ravindran

gururguru77@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 10 (2022): Vol 34 Issue 10, 2022

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-phenyl-propenone (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).

Keywords

Regioselective Tandem Michael Addition Aldol Addition Cyclohexanol Antibacterial activity
Suriyakala, T., Chinnaraj, A., Senthilkumar, V., Kamal Nasar, M., & Ravindran, G. (2022). Regioselective Synthesis and Antibacterial Studies of α,β-Unsaturated Ketone Substituted Cyclohexanols via Tandem Michael Addition-Aldol Addition-Cyclization Sequence under Solvent-Free Conditions. Asian Journal of Chemistry, 34(10), 2646–2650. https://doi.org/10.14233/ajchem.2022.23907
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