Preparation of some alpha, beta,gamma, delta, unsaturated carbonyl compounds and their derivatives with expected biological activity
JOURNAL OF EDUCATION AND SCIENCE,
2018, Volume 27, Issue 4, Pages 1-20
AbstractThis study includes the synthesis of the compound 2,3-diphenyl quinoxaline coupling ortho phenylenediamine with benzil which then banded with benzotriazole molecule through methylene bridge using formaldehyde in acidic medium to obtain 6-[(1H-benzotriazol-5-yl)methyl] 2,3-diphenylquinoxaline(1). Compound (1) was reacted with chloroacetophenone in presence of anhydrous potassium carbonate to form ketonic compound (2). Reaction of (2) with (4-nitrobenzaldehyde, 4-nitro acetophenone) through aldol condensation to obtain an carbonyl compounds (3-5), from which unsaturated ketones (6-8) were prepared and used as precursor for many heterocyclic derivatives such as oxiranes (9-11) when reacted with hydrogen peroxide and undergo mono bromination to compounds (12-14) by bromine in presence of base, and when react with hydrazine hydrate or phenyl hydrazine gave the pyrazoline compounds and their substituted compounds (15-20) and finally with hydroxyl amine hydrochloride gave the isooxazoline compounds (21-23).
The structure of these compounds were identified using physical properties and spectral methods (melting points, color change, infrared, ultraviolet and nuclear magnetic resonance spectra). Bromine tests were used to the detection of the unsaturated Ketones.
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