Synthesis and spectrophotometric analysis of 3,5-bis(arylidene)-4-piperidones

Lozanovski, Zlatko and Velkovski, Valentina (2026) Synthesis and spectrophotometric analysis of 3,5-bis(arylidene)-4-piperidones. In: 1st International Scientific Conference - Food Science, Nutrition, Innovative Technologies and Sustainability, 03.10.2025, Veles, North Macedonia.

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Abstract

Abstract

3,5-Bis(arylidene)-4-piperidones represent a class of synthetically accessible scaffolds with notable pharmacological potential, including anticancer, antimicrobial, and anti-inflammatory properties. In this study, three derivatives (3E,5E)-3,5-bis(2-fluorobenzylidene)-piperidin-4-one (IIIa), (3E,5E)-3,5-bis(2-bromobenzylidene)-piperidin-4-one (IIIb) and (3E,5E)-3,5-bis(2-trifluoromethylbenzylidene)-piperidin-4-one (IIIc) were synthesized via Claisen–Schmidt condensation of ortho-substituted aromatic aldehydes with 4-piperidone in methanol under basic conditions. Compounds were isolated as crystalline solids in good yields and characterized by melting-point analysis, UV-Vis, FTIR, ESI-MS, HPLC, and GC-MS.
FT-IR spectra confirmed conjugated carbonyl absorptions in the 1661–1676 cm⁻¹ range together with substituent-specific signals such as C–F, C–Br, and CF₃. Additional features, including aromatic C=C bands and a diagnostic trans =C–H vibration at ~965 cm⁻¹, supported their structural configuration. UV-Vis spectra displayed characteristic π→π* and n→π* transitions in the 228–370 nm region. The position of these bands reflected the electronic effects of the substituents, with CF₃ causing hypsochromic shifts and Br producing pronounced bathochromic shifts. These spectroscopic results confirm the successful synthesis and structural integrity of IIIa,IIIb and IIIc, highlighting their potential for further biological evaluation.
Given the electrophilic nature of their α,β-unsaturated carbonyl groups, these compounds also present opportunities for thiol-reactivity studies relevant to redox signaling, enzyme inhibition, and cellular stress response mechanisms.

Keywords: 4-piperidones, Claisen–Schmidt condensation, UV-Vis, FTIR, HPLC, GC-MS.

Item Type:	Conference or Workshop Item (Paper)
Uncontrolled Keywords:	analytical chemistry
Subjects:	Scientific Fields (Frascati) > Natural sciences > Chemical sciences
Divisions:	Higher Medical School
Depositing User:	PhD Zlatko Lozanovski
Date Deposited:	29 Aug 2026 20:22
Last Modified:	29 Aug 2026 20:22
URI:	https://eprints.uklo.edu.mk/id/eprint/11731

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