Synthesis, Characterization and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl- 4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate: Advanced Study

Salaheddine Boukhssas; Sara Hajib; Younas Aouine; Anouar Alami; Hassane Faraj; Abdelilah El Hallaoui

Salaheddine Boukhssas Doctoral Training �Bioactive Molecules, Health and Biotechnology�, Faculty of Sciences Dhar El Mahraz, Center of Doctoral Studies �Sciences and Technology�, Sidi Mohamed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco and Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Sara Hajib Doctoral Training �Bioactive Molecules, Health and Biotechnology�, Faculty of Sciences Dhar El Mahraz, Center of Doctoral Studies �Sciences and Technology�, Sidi Mohamed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco and Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Younas Aouine Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco and Department of Chemistry, Faculty of Sciences, Ibn Zohr University, P.B. 8106, Cit� Dakhla, Agadir 80060, Morocco.
Anouar Alami Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Hassane Faraj Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Abdelilah El Hallaoui Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.

Keywords: 1,2,3-triazole, ?-amino acid, oxazoline, antibacterial activity, 2D NMR

Abstract

The compound, diethyl 1-((4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate 2, was synthesized in high yield, through 1,3-dipolar cycloaddition reaction of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and diethyl but-2-ynedioate in the absence of a solvent. The structure of the synthesized compound was established on the basis of NMR spectroscopy (¹H, ¹³C), X-ray crystallography and MS data. The prepared compound was also tested in vitro for its antibacterial activity against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). The calculation of MBC/MIC ratio showed that this triazole derivative 2 had a bactericidal effect on the two strains tested.