Study of the Regioselectivity of the N-alkylation Reaction of 1H-1,2,4-Triazole

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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 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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