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Vol. 30 No. 3 (2018): Vol 30 Issue 3

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Microwave Synthesis and Antibacterial Activities of Some Imidazolidine Derivatives Containing 1,3,4-Oxadiazole Moiety

https://doi.org/10.14233/ajchem.2018.20970
Zeid Hassan Abood
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq
Hayder Raheem Ali
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq
Hussein Ali Qabel
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq
Osama Hameed Rasheed
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq

Corresponding Author(s) : Zeid Hassan Abood

zeid.ab2013@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 3 (2018): Vol 30 Issue 3

Abstract

5-(4-Aminophenyl)-2-thiol-1,3,4-oxadiazole (1) was synthesized via the reaction of carbon disulfide with 4-aminobenzoyl hydrazide in presence of potassium hydroxide in absolute ethanol. Compound 1 was converted to the corresponding diazonium salt which was introduced in coupling reaction with alkaline solution of 2-hydroxybenzaldehyde as coupling reagent to give azooxadiazole derivative 2 containing aldehyde group. The resulting aldehyde 2 was then introduced in condensation reactions with the primary aromatic amines including (4-bromoaniline, 4-chloroaniline, 4-nitroaniline, 3-nitroaniline, 4-methoxyaniline and 4-hydroxyaniline) using microwave irradiation technique in absolute ethanol to produce six imine derivatives of 1,3,4-oxadiazole (3a-f), respectively. Treatment of the resulting imines 3a-f with glycine using microwave irradiation in tetrahydrofuran afforded six new imidazolidines 4a-f substituted with 1,3,4-oxadiazole moiety, respectively. in vitro Antibacterial activity of the target compounds were investigated using two types of bacteria, Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). The results indicated that the newly synthesized imidazolidines (compounds 4d and 4f) showed enhanced activity against Gram-negative bacteria when compared with that of the control drug (gentamycin).

Keywords

Imidazolidines 1,3,4-Oxadiazoles Imines Antibacterial activity
Abood, Z. H., Ali, H. R., Qabel, H. A., & Rasheed, O. H. (2018). Microwave Synthesis and Antibacterial Activities of Some Imidazolidine Derivatives Containing 1,3,4-Oxadiazole Moiety. Asian Journal of Chemistry, 30(3), 546–550. https://doi.org/10.14233/ajchem.2018.20970
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