Diethyl [(4-{(9<i>H</i>-carbazol-9-yl)methyl}-1<i>H</i>-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate

Abstract

The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. 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 catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis.

Keywords

• triazole
• α-amino phosphonic ester
• click chemistry
• carbazole
• 2D-NMR spectroscopy