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.