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

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

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


Keywords


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

References


Willson, M.; Zinel, K.; Klaebe, A.; Periel J. J.; Baltz, T. Anti-trypanosomal compounds. Part II. Novel amidinium sulfinic compounds and phosphorylated heterocycles as anti-trypanosomal agents. Eur. J. Med. Chem. 1989, 24 (6), 623 – 625. https://doi.org/10.1016/0223-5234(89)90032-9.

Arnaud-Neu, F.; Boehmer, V.; Dozol, J.-F.; Gruettner, C.; Jakobi, R. A.; Kraft, D.; Mauprivez, O.; Rouquette, H.; Schwing-Weill, M.-J.; Simon, N.; Vogt, W. Calixarenes with diphenylphosphoryl acetamide functions at the upper rim. A new class of highly efficient extractants for lanthanides and actinides. J. Chem. Soc., Perkin Trans. 2 1996, 6, 1175 – 1182. https://doi.org/10.1039/P29960001175.

Vatsouro, I.; Serebryannikova, A.; Wang, L.; Hubscher-Bruder, V.; Shokova, E.; Bolte, M.; Arnaud-Neu, F.; Boehmer, V.; Kovalev, V. Narrow rim CMPO/adamantylcalix[4]arenes for the extraction of lanthanides and actinides. Tetrahedron 2011, 67 (42), 8092 – 8101. https://doi.org/10.1016/j.tet.2011.08.059.

Far, A. R.; Shivanyuk, A.; Rebek, J. Water-Stabilized Cavitands. J. Am. Chem. Soc. 2002, 124 (12), 2854 – 2855. https://doi.org/10.1021/ja012453p.

Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. Crystals version 12: software for guided crystal structure analysis. J. Appl. Crystallogr. 2003, 36 (6), 1487 – 1487. https://dx.doi.org/10.1107/S0021889803021800.

Sheldrick, G. M. A short history of shelx. Acta Crystallogr., Sect. A: Found. Adv. 2008, 64 (1), 112 – 122. https://doi.org/10.1107/S0108767307043930.




Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

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

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