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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 1 H -1,2,4-triazole with (4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl-4-methylbenzenesulfonate in presence of K 2 CO 3 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 N 1 -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 Labo...

Identification of the Regioselectivity of the Thermal Huisgen 1,3-Dipolar Cycloaddition Reaction between an Azide Derivative and a Synthetic Heterocyclic Alkyne, through a Comparative Study of NMR Spectral Data | Chapter 12 | Theory and Applications of Chemistry Vol. 4

The 1,3-dipolar cycloaddition reaction between 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and 9-(prop-2-ynyl)-9 H -carbazole, in toluene at reflux, leads to obtain two regioisomers with different proportions where the 1,4-regioisomer is generally more prominent than 1,5-regioisomer. The assignment of structures to 1,2,3-triazolic regioisomers was established in base of a comparative study of NMR spectral data ( 1 H, 13 C, 15 N and 2D 1 H- 15 N HMBC spectra) in addition to the elemental analysis and MS data. 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 a...

Synthesis and Characterization of 4-[(3,5-Dimethyl-1H-pyrazol-1-yl)Methyl]-4-Methyl-2-Phenyl-4,5-Dihydrooxazole| Chapter 11 | Theory and Applications of Chemistry Vol. 4

The compound, 4-[(3,5-dimethyl-1 H -pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyloxazoline derivative 1 , by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis of NMR spectroscopy ( 1 H, 13 C), MS data and elemental analysis. Author(s) Details Sara Hajib Doctoral Training “Bioactive Molecules, Health and Biotechnology”, Faculty of Sciences Dhar El Mahraz, Center of Doctoral Studies “Sciences and Technology”, LCO, Sidi Mohammed 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 ...

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 ...