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Abstract The original work of this thesis can be classified into two parts: Part I: Aims to the synthesis of 6-(4-methoxyphenyl)-4-oxo-2-thioxo-1, 2, 3, 4-tetrahydropyrimidine-5-carbonitrile 1 through the reaction of ethyl 2-cyano-3-(4-methoxyphenyl) acrylate with thiourea in presence of sodium ethoxide or by the one-pot cyclic condensation reaction of p-methoxy benzaldehyde, ethyl cyanoacetate and thiourea in ethanol containing anhydrous potassium carbonate. Study the behavior of 1 towards different electrophilic and nucleophilic reagents to synthesize new poly functionalized series of substituted pyrimidine-2-thione derivatives. The chloropyrimidine derivative 10 was utilized as starting material for preparation of new fused heterocyclic such as pyrimidoquinazoline derivative, 4-((4-acetylphenyl) amino)-6-(4-methoxyphenyl)-2-thioxo-1, 2-dihydropyrim- idine-5-carbonitrile, dithioxopyrimidine derivative, tetrazolopyrimidine derivative and 4-hydrazinyl pyrimidine derivative by reaction with anthranilic acid, p-aminoacetophenone, thiourea, sodium azide and hydrazine hydrate. The hydrazinyl pyrimidine derivative 6 was treated with electrophilic reagents such as ethyl chloroacetate, chloroacetyl chloride, ethyl chloroformate and acetylacetone gave the corresponding pyramidotriazine derivative 18, ethyl formate derivative 19 and diazolopyrimidine derivative 20 respectively. Also,-a-series-of 4-(4-methoxyphenyl)-6-oxo-2- (2-(substituted-benzylidene) hydrazinyl)-1, 6-dihydropyrimidine-5-carbonitrile derivatives 21a-d were prepared by the reaction of 4 with different aromatic aldehydes in glacial acetic acid. The reaction of Schiff’s base 21a with thioglycolic acid and chloroacetyl chloride afforded Oxothiazolidin derivative 22a and oxoazetidine derivative 23a respectively. Part II: This part aims to study the biological activities of the synthesized compounds as antioxidant, antimicrobial against Staphylococcus aureus (G+ve), Pseudomonas aeruginosa (G-ve), Candida albicans (yeast), Aspergillus niger (fungus) and anticancer against HePG2, HCT-116, MCF-7 cell lines. Keywords: quinazoline, tetrazolopyrimidine, pyrimidotriazine, oxothiazolidin, oxoazetidine, pharmacological and antimicrobial activities. |