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Abstract
The thesis is prefaced by a survey on th biological activity of aromatic and heteroaromatic thiosemicarbazone derivatives. The present invedtigation is concerned with the synthesis of 5-acetyl (or 5-benzoyl) 8-hydroxyquinoline-4-substituted thiosemicabazones in addition to cyclization of the thiosemicarbazone function into the corresponding thiazolidinone ring systems. The key intermediates , 5-acetyl (or 5-benzoyl)8-hydroxyquinoline was prepared via the reaction of 8-hydroxyquinoline and acetyl chloride or benzoyl chloride in the presence of anhydrous aluminum chloride as a catalyst in dichloroethane. Thiosemicarbazides (Ia-1)were prepared by reaction of an aryl or alkyl isothiocyanate and hydrazine hydrate. 5-Acetyl (or 5-Benzoyl)-8-hydroxyquinoline-4-substituted thiosemicarbazones (IIa-m, IIIa-m) were prepared through condensation of 5-acetyl ( or 5-benzoyl)-8-hydroxyquinoline with appropraite 4-substituted-3-thiosemicabazides (Ia-1) in acidified ethanol. The thiosemicarbazones (IIa-1, IIIa-f) were cyclized into corresponding thiazolidinones (IV a-l, Va-f) by reaction with ethylbromoacetate in the presence of anhydrous sodium acetate in absolute ethanol.