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

Authors

  • Oleksandra O. Chaikovska Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine
  • Radomyr V. Smaliy Enamine Ltd, Ukraine
  • Nataliya A. Shtyl Enamine Ltd, Ukraine
  • Oleksandr M. Кostyuk Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.20.206316

Keywords:

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

Abstract

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

Supporting Agencies

  • NASU theme «Phosphine and carbene polydentate ligands
  • synthesis and application» (state registration № 0116U008796
  • 2016 – 2021 years)

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References

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Published

2020-09-18

How to Cite

(1)
Chaikovska, O. O.; Smaliy, R. V.; Shtyl, N. A.; Кostyuk O. M. P-Nitrophenyl Ester of (diphenylphosphoryl)acetic Acid As a Reagent for the Synthesis of 2-(phosphorylmethyl)benzimidazole. J. Org. Pharm. Chem. 2020, 18, 39-42.

Issue

Vol. 18 No. 3(71) (2020)

Section

Original Researches

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