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Abstract This present thesis In this investigation 4-hydroxyquinolinone derivatives were used as a versatile starting materials as products that might have higher potency and good biological activity. 3-Acetyl-6-nitro-4-hydroxy-1-methyl (or ethyl)-2-quinolinone (2a,b) were prepared by nitration by using conc. H2SO4 / HNO3 in the presence of KNO3. 3-Acetyl-6-nitro-4-hydroxyquinolinone derivatives (2a,b) reacted with α,β-unsaturated nitriles to give 4H-pyrano[3,2-c]quinolinone derivatives(6a-l) . Reaction of 3-acetyl-6-nitro-4-hydroxyquinolinone compounds (2a,b) with ethyl cyanoacetate or malono-nitrile in presence of formaldehyde or acetaldehyde yielded corresponding 4H-pyrano[3,2-c]quinolinone derivatives (9a-g). These compounds (2a,b) were allowed to react with malononitrile in glacial acetic acid give pyrano[3,2-c]quinolinone (10a,b) which reacted with α,β-nitriles to yield 6H-isochromeno[4,3-c]quinolone derivatives (11a-d) and (12a-d). Reaction of 3-acetyl-6-nitro-4-hydroxy-2-quinolin-ones (2a,b) and malononitrile with sulphur element4H-thiopyrano[3,2- b]pyridine derivatives (19a-b). Treatment of the acetyl derivatives (2a,b) with sulphuryl chloride in dioxane afforded the corresponding diacetyl derivatives (20a,b). Reaction of the latter product with aqueous sodium cyanide or sodium azide yielded furoquinolinones (21a,b) and tetrazoloylquinolones (23a,b). Condensation of (2a,b) with aromatic aldehydes afforded corresponding Schiff’s bases (24a-d). Reaction of compounds (2a,b) with aromatic and aliphatic amines to yield the Schiff’s bases (25a-j) Refluxing compounds (2a,b) with urea ,thiourea and semicarbazide derivatives in boiling DMF give compounds (26a-f). Reactivity of compounds (2a,b) were extended to include their reaction with dimmer amines, e.g., p-phenylene diamine and ethylene diamine in ethanol to give azomethine derivatives (27a-d). |