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
Theory and Applications of Chemistry Vol. 4,
Page 125-132
Abstract
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.
Keywords:
- Oxazoline
- 1H-1,2,4-triazole
- β-aminoalcohol
- α-amino acid
- 2D heteronuclear NMR experiments
How to Cite
Aouine, Y., Boukhssas, S., Alami, A., Faraj, H., & Hallaoui, A. E. (2020). 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. Theory and Applications of Chemistry Vol. 4, 125-132. Retrieved from https://stm1.bookpi.org/index.php/tac-v4/article/view/1107
- Abstract View: 0 times