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New Imidazolidineiminothione, Imidazolidin-2-one and Imidazoquinoxaline 
 Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities

View Article: PubMed Central - PubMed

ABSTRACT

3334.3568331112,(11c)(3f): A series of new 5-imino-4-thioxo-2-imidazolidinone derivatives with various halogenated and alkylated aromatic substituents at N1 and N3 was synthesized. Imidazolidineiminothione derivatives were prepared from the reaction of N-arylcyanothioformamide derivatives with aryl isocyanates. These compounds were used as key synthons for the preparation of wide variety of new substituted imidazole compounds. Imine hydrolysis of with ethanolic HCl produced the corresponding 4-thioxo-2,5-imidazolidindiones Condensation of with benzophenonhydrazone furnished the corresponding 4-azine derivatives . Monohydrazono and dihydrazono derivatives and were obtained upon treatment of imidazolidinone derivatives with hydrazine hydrate. Finally, imidazolidinones were reacted with o-phenylenediamines or pyrazol-5(4H)-ones and afforded the corresponding imidazoquinoxaline and imidazolidin-4-ylidenepyrazolone-5(4H)-one derivatives and respectively. Evaluation of the antibacterial and antifungal activities for the synthesized compounds was carried out to probe their activities. Most of the tested compounds showed significant activities. The best antimicrobial activity was observed for 1-(3-ethoxyphenyl)-6-methyl-1-phenyl-1H-imidazo[4,5-b]quinoxalin-2(3H)-ones followed by 5-imino-3-(3-methoxy- phenyl)-1-phenyl-4-thioxoimidazolidin-2-one .

No MeSH data available.


Reactions of imidazolidineiminothione derivatives with different reagents.
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S3: Reactions of imidazolidineiminothione derivatives with different reagents.

Mentions: neiminothiones toward carbon nucleophiles. Thus, condensation of the imidazolidineiminothiones 3c,i with 3-methyl-1H-pyrazol-5(4H)-one derivatives in boiling ethanol using triethylamine as a basic catalyst afforded a product which was identified as imidazolidin-4-ylidenpyrazolones 12a-d (Scheme 3 ). IR spectrum of 12d as a representative example revealed absorption bands at: 3280, 1717 and 1603 characteristic to NH, C=O and C=N functional groups, respectively. The 1H NMR spectrum exhibited triplet, quartet and singlet at: 1.14, 4.19 and 2.41 ppm due to ethoxy and methyl protons, singlet signal at 12.83 specific for NH. Moreover, its 13C NMR spectrum revealed signals at: 14.8, 15.1, 63.3 assigned ethoxy and methyl carbons signals 105.0, 144.7 corresponding for C=C and signals at 159.3, 159.4, 162.3 and 166.6 assigned to 2 imino and 2 carbonyl carbons.


New Imidazolidineiminothione, Imidazolidin-2-one and Imidazoquinoxaline 
 Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities
Reactions of imidazolidineiminothione derivatives with different reagents.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4997951&req=5

S3: Reactions of imidazolidineiminothione derivatives with different reagents.
Mentions: neiminothiones toward carbon nucleophiles. Thus, condensation of the imidazolidineiminothiones 3c,i with 3-methyl-1H-pyrazol-5(4H)-one derivatives in boiling ethanol using triethylamine as a basic catalyst afforded a product which was identified as imidazolidin-4-ylidenpyrazolones 12a-d (Scheme 3 ). IR spectrum of 12d as a representative example revealed absorption bands at: 3280, 1717 and 1603 characteristic to NH, C=O and C=N functional groups, respectively. The 1H NMR spectrum exhibited triplet, quartet and singlet at: 1.14, 4.19 and 2.41 ppm due to ethoxy and methyl protons, singlet signal at 12.83 specific for NH. Moreover, its 13C NMR spectrum revealed signals at: 14.8, 15.1, 63.3 assigned ethoxy and methyl carbons signals 105.0, 144.7 corresponding for C=C and signals at 159.3, 159.4, 162.3 and 166.6 assigned to 2 imino and 2 carbonyl carbons.

View Article: PubMed Central - PubMed

ABSTRACT

3334.3568331112,(11c)(3f): A series of new 5-imino-4-thioxo-2-imidazolidinone derivatives with various halogenated and alkylated aromatic substituents at N1 and N3 was synthesized. Imidazolidineiminothione derivatives were prepared from the reaction of N-arylcyanothioformamide derivatives with aryl isocyanates. These compounds were used as key synthons for the preparation of wide variety of new substituted imidazole compounds. Imine hydrolysis of with ethanolic HCl produced the corresponding 4-thioxo-2,5-imidazolidindiones Condensation of with benzophenonhydrazone furnished the corresponding 4-azine derivatives . Monohydrazono and dihydrazono derivatives and were obtained upon treatment of imidazolidinone derivatives with hydrazine hydrate. Finally, imidazolidinones were reacted with o-phenylenediamines or pyrazol-5(4H)-ones and afforded the corresponding imidazoquinoxaline and imidazolidin-4-ylidenepyrazolone-5(4H)-one derivatives and respectively. Evaluation of the antibacterial and antifungal activities for the synthesized compounds was carried out to probe their activities. Most of the tested compounds showed significant activities. The best antimicrobial activity was observed for 1-(3-ethoxyphenyl)-6-methyl-1-phenyl-1H-imidazo[4,5-b]quinoxalin-2(3H)-ones followed by 5-imino-3-(3-methoxy- phenyl)-1-phenyl-4-thioxoimidazolidin-2-one .

No MeSH data available.