p-Nitrophenyl ester of (diphenylphosphoryl)acetic acid as a reagent for the synthesis of 2-(phosphorylmethyl)benzimidazole
Aim. To expand the synthetic potential of the activated esters of diphenylphosphorylacetic acid for the synthesis of phosphorylated benzimidazoles.
Results and discussion. A new synthetic pathway to obtain 2-((diphenylphosphoryl)methyl]-1H-benzimidazole has been found via the reaction of p-nitrophenyl ester of (diphenylphosphoryl)acetic acid and o-phenylenediamine. The complexing ability of 2-[(diphenylphosphoryl)methyl]-1H-benzimidazole for metal ions of the twelvth group has been determined. The chelate complex with CdCl2 has been prepared and studied by the X-ray diffraction method.
Experimental part. The two-step reaction of p-nitrophenyl ester of (diphenylphosphoryl)acetic acid with o-phenylenediamine resulted in 2-[(diphenylphosphoryl)methyl]-1H-benzimidazole with a high yield. Its complex with CdCl2 was synthesized. Molecular structures of all compounds prepared were confirmed by the methods of 1H and 13C NMR spectroscopy, LC/MS spectrometry, elemental analysis; for the CdCl2 complex – by the data of X-ray diffraction analysis.
Conclusions. A new synthetic approach to obtain 2-(phosphorylmethyl)benzimidazole via the reaction of the activated ester of phosphorylacetic acid and o-phenylenediamine has been carried out. It has been shown that 2-[(diphenylphosphoryl)methyl]-1H-benzimidazole is capable of forming chelating complexes with the salts of cadmium in the neutral medium.
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Abbreviated key title: J. Org. Pharm. Chem.
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