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
Farouk, Osama; Magdy A. Ibrahim; Nasser M. El-Gohary;
Abstract
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. b-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 b-chloroenaldehyde
1 with some 1,3-C,N-binucleophiles produced pyridines,
pyrido[1,2-a]benzimidazole, pyrazolo[3,4-b]pyridine and pyrido[2,3-
d]pyrimidine incorporating pyrimidine moiety through NH linkage.
Condensation of b-chloroenaldehyde 1 with some cyclic active
methylene compounds namely dimedone and barbituric acid
afforded chromen-2-ylaminopyrimidine and pyrano[2,3-d]pyrimidine.
Moreover, b-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.
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. b-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 b-chloroenaldehyde
1 with some 1,3-C,N-binucleophiles produced pyridines,
pyrido[1,2-a]benzimidazole, pyrazolo[3,4-b]pyridine and pyrido[2,3-
d]pyrimidine incorporating pyrimidine moiety through NH linkage.
Condensation of b-chloroenaldehyde 1 with some cyclic active
methylene compounds namely dimedone and barbituric acid
afforded chromen-2-ylaminopyrimidine and pyrano[2,3-d]pyrimidine.
Moreover, b-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.
Other data
Title | 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 | Authors | Farouk, Osama ; Magdy A. Ibrahim; Nasser M. El-Gohary | Issue Date | Dec-2021 | Journal | An International Journal for Rapid Communication of Synthetic Organic Chemistry | Volume | 51 | Issue | 24 | Start page | 3805 | End page | 3817 |
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