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The biheterocyclic derivative of the phosphonic glycine analogue is prepared selectively by reaction between the α-azidoamino diethyl methylphosphonate and the 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole. The dipolar -1,3 cycloaddition reaction using Click Chemistry was carried out in a solvent water/ethanol mixture in a ratio of 1:1. Copper sulphate pentahydrate and sodium ascorbate are used in the reaction in catalytic amounts. The compound [diethyl [{4-[(1H-benzo[d]imidazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}(benzamido) methyl] phosphonate was isolated pure as a white powder, after chromatography on a silica gel column (ethyl acetate/hexane acetate: 1/1). The yield of pure product is 90%, after recrystallization in an ether/hexane mixture. The structure of the -1,4 isomer is attributed to the compound obtained by means of 1D and 2D NMR and based on data from the literature concerning the cycloaddition reaction via Click Chemistry. Two-dimensional NMR spectroscopy played a major role. The analysis of the different correlations between adjacent hydrogens and carbons, and also between hydrogens and distant carbons, confirmed the proposed structure.

european journal of advanced chemistry research

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments