p-Nitrophenyl ester of (diphenylphosphoryl)acetic acid as a reagent for the synthesis of 2-(phosphorylmethyl)benzimidazole

Oleksandra O. Chaikovska, Radomyr V. Smaliy, Nataliya A. Shtyl, Oleksandr M. Кostyuk


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.

Received: 25.06.2020

Revised: 18.07.2020

Accepted: 27.08.2020


p-nitrophenyl ester of (diphenylphosphoryl)acetic acid; phosphorylated benzimidazoles


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Abbreviated key title: J. Org. Pharm. Chem.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)