Research Article

Synthesis and Structural Determination of Two New tri-Heterocyclic Regioisomeric Compounds, Precursors of Bi-Triazolic α-Amino Acids, via a Comparative Study using 1D NMR Spectroscopy

S. Hajib
Sidi Mohammed Ben Abdellah University, Morocco
A. Ksakas
Catalysis and Environment Laboratory, Morocco
Y. Aouine
Ibn Zohr University, Morocco
A. Alami
Sidi Mohammed Ben Abdellah University, Morocco
* Corresponding author
H. Faraj
Sidi Mohammed Ben Abdellah University, Morocco
DOI icon 10.24018/ejchem.2020.1.6.36

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Submitted 2020-12-07
Published 2020-12-22

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Article Main Content

In this article, we describe the synthesis of two new triheterocyclic regioisomers, named 4-({4-[(1H-1,2,4-triazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}methyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole and 4-({5-[(1H-1,2,4-triazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}methyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole. The action of 1-(propargyl)-1H-1,2,4-triazole on 4-(azidomethyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole, in a very small quantity of toluene, led after 48 hours at 120 °C to two regioisomers with an overall yield of 90%. The allocation of structures to these two regioisomers was carried out based on a comparative spectroscopic study using 1D NMR of the proton and carbon 13, as well as based on data from the literature concerning the cycloaddition reaction.

Keywords: Azide 1,3-dipolar cycloaddition 1D NMR spectroscopic study oxazoline derivatives 1,4-regioisomer 1,5-regioisomer 1,2,3-triazole 1,2,4-triazole

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