الفهرس 
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Abstract
Alkylation of 4,6-diamino-3-cyanopyridine-2(1H)-thione (1) with active halo compounds namely; ethyl chloroacetate, chloroacetic acid, 2-chloro-N-phenylacetamide, chloroacetonitrile or chloroacetamide gave the corresponding S-alkyl derivatives 3, 5, 6, 8 and 10, respectively. Thienopyridines 4, 7, 9 and 11 were synthesized via the reaction of compound 1 with respective halo compound in hot KOH or via cyclization of S-alkyl derivatives 3, 5, 6, 8 and 10, respectively with hot KOH solution. The reaction of compound 1 with 3-bromopentane-2,4-dione or ethyl 2-bromo-3-oxobutanoate afforded 2-acetylthienopyridine 12. Treatment of compound 1 with 2-bromo-1-phenylethylidenemalono-nitrile or acrylonitrile afforded pyrido[2’,3’:4,5]thieno[2,3-b]pyridine 13 and S-alkyl derivative 14. 1-Thia-3,5,8-triazaacenaphthylene 15 was obtained via reaction of compound 4 with carbon disulfide or phenyl isothiocyanate. 4,6-Diamino-3-cyano-2-(methylthio)pyridine (2) reacted with ethyl chloroformate, phenyl isothiocyanate, (4,6-dimethylpyrimidin-2-yl)cyanamide, acetic acid or chloroacetyl chloride to afford the corresponding carbamate 16, phenylthiourea 17, guanidine 18, acetamide 19 and chloroacetamide 20, respectively. Also, compound 2 was subjected to react with acetylacetone, ethyl benzoylacetate, ethyl
Abstract iii
acetoacetate, diethyl malonate, or diethyl oxalate to yield the corresponding pentenonylamino derivative 21 and amides 22-25, respectively. Treatment of compound 2 with bromine, sulfuryl chloride, formaldehyde or aromatic diazonium salts gave 5-bromopyridine 26, 5-chloropyridine 27, methylenebispyridine derivative 28 and azo dye compounds 29-32, respectively. Compound 2 was treated with potassium hydroxide or hydrazine hydrate to afford the corresponding nicotinamide 33 and pyrazolo[3,4-b]pyridine 34, respectively. Treatment of chloroacetamide 20 with thiols, secondary amines, potassium thiocyanate, active methylenes, potassium 1-anilino-2,2-dicyanoethenethiolate, 4,6-di-amino-2-mercaptonicotinonitrile and 2-amino-6-mercapto-4-phenyl-pyri-dine-3,5-dicarbonitrile yielded the corresponding S-alkyl 35-40, N-alkyl 41-46, imidazole 47, pyrroles 48-50, thiophene 51 and thienopyridines 52, 53, respectively. Arylhydrazones 54-57 and thiobutanamidopyridine derivative 58 were obtained via treatment of butanamide 23 with aromatic and heterocyclic diazonium salts or phenyl isothiocyanate. Reaction of butanamide 23 with urea or thiourea and aromatic aldehyde afforded 1,8-naphthyridine derivative 59 and pyrimidines 60-65, respectively. Compound 2 reacted with dimethylformamide dimethylacetal to give N,N-dimethylimidoformamide 66, which treated with secondary amines namely; piperidine and piperazine to afford substituted methyleneamino-pyridines 67 and 68, respectively. Treatment of compound 66 with cyanothioacetamide or cyclohexane-1,3-dione, malononitrile, ethyl cyanoacetate and 2-aminoprop-1-ene-1,1,3-tricarbonitrile gave cyano-propenethioamide 69, cyclohexylideneaminopyridine-dione 70 and the corresponding naphthyridine derivatives 71-73, respectively.
Abstract iv
Most of products gave good activity, when evaluated for anti-inflammatory, antibacterial and antifungal activity. Keywords: 4,6-Diaminopyridine, Methylthiopyridine, S-alkylation, N-alkylation, Thienopyridine, Pyrazolopyridine, Chloroacetamide, Butanamide, Imidazole, Thiophene, Pyrroles, Azo dye compounds, Arylhydrazones, Pyrimidines, Anti-inflammatory, Antibacterial, Antifungal