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Vol. 30 No. 1 (2018): Vol 30 Issue 1

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Microwave Synthesis and Antibacterial Activities of New Imidazolidines Derived from 2-Aminobenzothiazole

https://doi.org/10.14233/ajchem.2018.20936
Zeid Hassan Abood
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq
Hussein Ali Qabel
Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq
Hayder Raheem Ali
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. 1 (2018): Vol 30 Issue 1

Abstract

2-Aminobenzothiazole (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 azo-benzothiazole derivative (2) bearing aldehyde group. The resulting aldehyde (2) was introduced in condensation reactions with the primary aromatic amines including (4-nitroaniline, 3-nitroaniline, 4-hydroxyaniline, 4-methoxyaniline, 2-methoxyaniline, 4-bromoaniline, 4-chloroaniline and 2,4-dichloroaniline) using microwave irradiation technique in absolute ethanol to produce eight imine derivatives of benzothiazole (3a-h), respectively. Treatment of the resulting imines (3a-h) with glycine using microwave irradiation in tetrahydrofuran afforded eight new imidazolidines (4a-h) substituted with benzothiazole moiety, respectively. Preliminary 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 4a, 4b, 4c, 4d, 4e, 4g and 4h) exhibited greater activities than gentamycin against Gram-positive bacteria. On the other hand, compounds 4d and 4h were also showed better activities against Gram-negative bacteria when compared with that of the control drug (gentamycin).

Keywords

Imidazolidines Imines Benzothiazoles Azo Antibacterial activity
Abood, Z. H., Qabel, H. A., Ali, H. R., & Rasheed, O. H. (2017). Microwave Synthesis and Antibacterial Activities of New Imidazolidines Derived from 2-Aminobenzothiazole. Asian Journal of Chemistry, 30(1), 133–137. https://doi.org/10.14233/ajchem.2018.20936
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