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

  • 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.
  • 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.
  • 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: Oxazoline, 1,2,3-triazole, 1,3-dipolar cycloaddition, 1H-15N correlation

Abstract

The 1,3-dipolar cycloaddition reaction between 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and 9-(prop-2-ynyl)-9H-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 (1H, 13C, 15N and 2D 1H-15N HMBC spectra) in addition to the elemental analysis and MS data.

Published
2020-03-07
How to Cite
Aouine, Y., Boukhssas, S., Alami, A., Faraj, H., & Hallaoui, A. E. (2020). 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. Theory and Applications of Chemistry Vol. 4, 116-124. Retrieved from https://stm1.bookpi.org/index.php/tac-v4/article/view/1106
Issue
Theory and Applications of Chemistry Vol. 4
Section
Chapters