Synthesis of Some New Pyrimidines and Pyrrolo [2,3-d] Pyrimidines as Potential Antimicrobial Agents

CYCLOCONDENSATION reaction of compound 1 with oxalyl choloride in acetone and dimethyl formamide afforded pyrrolo [2,3-d] pyrimidine derivative 2, which was reacted with p-amino acetophenone, p-aminobenzenesulfonamide (sulpha drugs), thiosemicarbazide, ethyl chloroacetate and benzoyl acetonitrile to give compounds 3, 4a-c, 5, 6, and 7, respectively. Condensation reaction of acetyl derivative 3 with 3, 4, 5-trimethoxybenzaldehyde afforded compound 8. 2(1H)-pyridone and imino pyridine derivatives 9, 10 were obtained by the reaction of compound 8 with ethyl cyanoacetate or malononitrile in presence of ammonium acetate. Moreover, chalcone derivative 8 was condensed with thiourea to give compound 11. Michel condensation reaction of 3 with ethyl cyanoacetate and 3-indolcaroxaldehyde leads to the formation of the pyridine 12 in one step reaction. Bromination of compound 13 afforded 14, which was reacted with thiourea to give compound 15. Furthermore, compound 13 was allowed to react with hydroxyl amine hydrochloride and phenyl hydrazine to give compounds 16 and 17, respectively. The antimicrobial activity of some of synthesized compounds was evaluated.