Utility of 2-[(1-chloro-3-oxoprop-1-en-1-yl)amino]-4-(4-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile for construction of some new heterocyclic systems as antimicrobial agents

The electron deficient substrate; 2-[(1-chloro-3-oxoprop-1-en-1-yl)amino]-4-(4-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile (1) was utilized as building block for construction of some novel heterocyclic rings bearing pyrimidine nucleus. beta-Chloroenaldehyde derivative 1 was allowed to react with a diversity of 1,3-N,N-binucleophilic reagents producing some heterocyclic systems namely triazolo[4,3-a]pyrimidine, pyrimido[1,2-a]benzimidazole, pyrimido[1,2-a]pyrimidine and pyrimido[2,1-c][1,2,4]triazine. Reaction of beta-chloroenaldehyde 1 with some 1,3-C,N-binucleophiles produced pyridines, pyrido[1,2-albenzimidazole, pyrazolo[3,4-b]pyridine and pyrido[2,3-d]pyrimidine incorporating pyrimidine moiety through NH linkage. Condensation of beta-chloroenaldehyde 1 with some cyclic active methylene compounds namely dimedone and barbituric acid afforded chromen-2-ylaminopyrimidine and pyrano[2,3-d]pyrimidine. Moreover, beta-chloroenaldehyde 1 reacted with some 1,4-binucleophiles namely o-phenylenediamine, 1,6-diaminopyridone, o-aminophenol and o-aminothiophenol leading to benzodiazepine, pyrido[1,2-b][1,2,4]triazepine, benzoxazepine and benzothiazepine bearing the pyrimidine moiety through NH linkage. The antimicrobial evaluation of the synthesized compounds appeared variable inhibitory effect toward the tested microorganisms. Structures of the new synthesized products were established based on their analytical and spectral data. [GRAPHICS] .

Automated summary

In this study, the electron deficient substrate 1 was utilized for the construction of novel heterocyclic rings bearing pyrimidine nucleus. The synthesized compounds exhibited variable inhibitory effect towards tested microorganisms, suggesting potential antimicrobial properties. The structures of the new synthesized products were established based on their analytical and spectral data.