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.
Highlights
For several decades, in the face of microbial resistance to antibiotics, there has been a strong rush to synthesize organophosphorus compounds [1], which are considered to be new bioisosters of amino carboxylic acids
The biheterocyclic derivative of the phosphonic analog phosphonic analog of glycine was obtained with an excellent yield (90%), as a white solid after of glycine was obtained with an
The characterization of the structure of the diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido) methyl]phosphonate was performed by different spectroscopic methods and elemental analysis
Summary
In the face of microbial resistance to antibiotics, there has been a strong rush to synthesize organophosphorus compounds [1], which are considered to be new bioisosters of amino carboxylic acids. Important biological and environmental properties of heterocyclic phosphonic amino acids have been identified in the literature [3]. They proved their relevance in the design of new formulae for osteoporosis drugs [4], as antimicrobial and antioxidant agents [5,6], anticancer compounds [7], and antibacterial compounds [8], and in the study of corrosion inhibition [9,10]. Methods for the synthesis of phosphonic amino acids bearing a heterocycle in the alpha position have been described [11,12]. Their triazolic analogs remain very limited [13]. Continuing our investigations on the synthesis of heterocyclic phosphonic [14], we described in this paper our results concerning the synthesis of a new biheterocyclic phosphonic amino ester, namely diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate
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