Study of the Regioselectivity of the N-alkylation Reaction of 1H-1,2,4-Triazole with an O-tosyl Derivative, Using Two-Dimensional NMR Spectroscopy| Chapter 13 | Theory and Applications of Chemistry Vol. 4

The alkylation reaction of 1H-1,2,4-triazole with (4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl-4-methylbenzenesulfonate in presence of K2CO3 as base and a catalytic amount of tetrabutylammonium bromide in N,N’-dimethylformamide, followed by an oxazoline ring-opening reaction in an acidic medium, and protection of amine function, leads normally to obtain two regioisomers of N-protected β-aminoalcohols with prevalence of the N1-isomer. After purification by column chromatography of the crude reaction product, only a single product is obtained in 97% yield. Hence, there is need of its identification by spectroscopic study.

Author(s) Details

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, Cité Dakhla, Agadir 80060, Morocco.

Salaheddine Boukhssas
Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco and Doctoral Training “Bioactive Molecules, Health and Biotechnology”, Center of Doctoral Studies “Sciences and Technology”, Faculty of Sciences Dhar El Mahraz, Sidi Mohamed Ben Abdellah University, P.B. 2626, Fez 30000, 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

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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| Chapter 8|Theory and Applications of Chemistry Vol. 4

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.

Author(s) Details

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.

View Book – http://bp.bookpi.org/index.php/bpi/catalog/book/149