Synthèse Et Caractérisation De La Structure Du [{4-[(1HBenzo[D]Imidazol-1-Yl)Méthyl]- 1H-1,2,3-Triazol-1 Yl}(Benzamido)Méthyl]Phospho nate De Diéthyle Par La Spectroscopie RMN 1D Et 2D

Le compose [{4-[(1H-benzo[d]imidazol1-yl)methyl]-1H-1,2,3-triazol-1- yl}(benzamido) methyl] phosphonate de diethyle ester synthetise de facon regioselective, par une reaction de cycloaddition dipolaire -1,3 entre l’αazidoamino methylphosphonate de diethyle et le 1-(prop-2-yn-1-yl)-1Hbenzo[d]imidazole. La reaction de cyclisation par Chimie click est realisee dans un melange de solvant eau/ethanol (50/50) en presence de sulfate de cuivre pentahydrate et de l’ascorbate de sodium en quantite catalytique. Le derive biheterocyclique de l’analogue phosphonique de la glycine est ainsi obtenu avec un excellent rendement (90%), sous forme de solide blanc apres chromatographie sur colonne de gel de silice (acetate d’ethyle/hexane : 1/1) et recristallisation dans un melange ether/hexane. La caracterisation de la structure attribuee de l’isomere -1,4, a ete realisee par le biais de la spectroscopie RMN 1D et 2D ainsi que sur la base des donnees de la litterature concernant la reaction de cycloaddition par Chimie Click. La 2D Spectroscopie RMN a joue un role fondamentale grâce aux differentes correlations observees entre les hydrogenes et les carbones adjacents et aussi entre les hydrogenes et les carbones lointains. The compound, diethyl [{4-[(1H-benzo[d]imidazol-1-yl)methyl]-1H1,2,3-triazol-1-yl} (benzamido)methyl]phosphonate, was prepared in a regioselective manner, through 1,3-dipolar cycloaddition reaction between αazidoaminomethyl phosphonate and 1-(prop-2-yn-1-yl)-1Hbenzo[d]imidazole. The cyclization reaction by click chemistry was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and sodium ascorbate in catalytic quantities. The biheterocyclic derivative of the phosphonic analog of glycine was obtained with an excellent yield (90%), as a white solid after chromatography on a silica gel column (ethyl acetate/hexane: 1/1) and recrystallization in an ether/hexane mixture. The characterization of the structure of the resulting 1,4-isomer was performed by 1D and 2D NMR spectroscopy as well as on the basis of data from the literature concerning the cycloaddition reaction by Chemistry Click. The 2D NMR Spectroscopy played a fundamental role through different correlations observed between the hydrogens and adjacent carbons and also between hydrogens and distant carbons.