Traditional, one-pot three-component synthesis and anti-bacterial evaluations of some new pyrimidine derivatives

Abstract

In this study, a novel series of pyrimidine compounds featuring azo linkages was synthesized via a sequence of stepwise and one-pot three-component reactions. The synthetic process commenced with the diazotization of 3-chloro-4-methyl aniline, followed bycoupling reaction with 4-hydroxy acetophenone, yielding the azo molecule denoted as 1-(3-((3-chloro-4-methylphenyl)diazenyl)-4-hydroxyphenyl)ethan-1-one. Subsequently, this compound underwent benzylation with benzyl bromide by Williamson ether synthesis, leading to the formation of 1-(4-(benzyloxy)-3-((3-chloro-4-methylphenyl)diazenyl)phenyl)ethan-1-one. The resultant azo-benzyloxy compound was then subjected to both classical and one-pot methodologies to synthesize pyrimidine derivatives, from results obtained from one pot reaction were in good yield. Structural elucidation of the newly synthesized compounds was characterized by spectral analysis, including FT-IR, 1H NMR, 13C NMR, and 13C-DEPT-135-NMR. The spectroscopic data confirmed the integrity of the molecular structures. Lastly, certain pyrimidine derivatives were evaluated for their antimicrobial activity against two strains of bacteria, namely Staphylococcus aureus and Escherichia coli. The results revealed that as the increasing of concentration, the sensitivity increased as reached 800 µg /mL no growth of bacterial was seen, It is also notable that the synthesized compounds have antimicrobial efficacy against both bacterial types.