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2-(2-Hydroxyphenyl)imidazolidines and their O-phosphorylated derivatives

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Abstract

2-(2-Hydroxyaryl)imidazolidines were synthesized by reaction of aromatic carbonyl compounds with N,N′-dialkylethylenediamines. The title compounds were also prepared using the corresponding Schiff bases instead of carbonyl compounds. Phosphorylation of 2-(2-hydroxyphenyl)imidazolidines with phosphoryl and phosphorothioyl chlorides and phosphorochloridites was accomplished. The reaction of O-phosphorylsalicylaldehyde with N,N′-dialkylethylenediamines also afforded 2-(2-hydroxyphenyl)imidazolidines.

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References

  1. Marki, F., Buch, O., Delini-Stula, A., Kraetz, J., Petermann, H., Radeka, E., Schweizer, A., Thomann, P., and Truog, A., Arzneim. Forsch., 1984, vol. 34, no. 3, p. 247.

    CAS  Google Scholar 

  2. Sharma, V. and Khan, M., Eur. J. Med. Chem., 2001, vol. 36, no. 3, p. 651. doi 10.1016/S0223-5234(01)01256-9

    Article  CAS  Google Scholar 

  3. Caterina, M.C., Perillo, I.A., Boiani, L., Pezaroglo, H., Cerecetto, H., Gonzalez, M., and Salerno, A., Bioorg. Med. Chem., 2008, vol. 16, no. 5, p. 2226. doi 10.1016/j.bmc.2007.11.077

    Article  CAS  Google Scholar 

  4. Saczewski, J., Hudson, A.L., and Rybczynska, A., Acta Pol. Pharm. Drug Res., 2009, vol. 66, no. 6, p. 671.

    CAS  Google Scholar 

  5. Neves, J.K., Parasitol. Res., 2010, vol. 107, no. 3, p. 531. doi 10.1007/s00436-010-1886-y

    Article  Google Scholar 

  6. Gleave, R.J., Walter, D.S., Beswick, P.J., Fonfria, E., Michel, A.D., and Roman, S.A., Bioorg. Med. Chem. Lett., 2010, vol. 20, no. 16, p. 4951. doi 10.1016/j.bmcl.2010.05.018

    Article  CAS  Google Scholar 

  7. Chemosensors: Principles, Strategies, and Applications, Wang, B. and Anslyn, E.V., Eds., Hoboken NJ: Wiley, 2011, p. 371. doi 10.1002/9781118019580

  8. Lakowicz, J.R. and Geddes, C.D., Top. Fluoresc. Spectrosc., 2005, vol. 9, p. 59.

    Article  Google Scholar 

  9. Jurcik, V. and Wilhelm, R., Tetrahedron, 2004, vol. 60, no. 14, p. 3205. doi 10.1016/j.tet.2004.02.021

    Article  CAS  Google Scholar 

  10. Buchs, B., Godin, G., Trachsel, A., de Saint Laumer, J.-Y., Lehn, J.-M., and Herrmann, A., Eur. J. Org. Chem., 2011, no. 4, p. 681. doi 10.1002/ejoc.201001433

    Article  Google Scholar 

  11. Eckstein, Z. and Lukasiewicz, A., Przem. Chem., 1960, vol. 39, p. 367.

    CAS  Google Scholar 

  12. Bagautdinova, R.Kh., Pudovik, E.M., Burilov, A.R., and Pudovik, M.A., Russ. J. Gen. Chem., 2015, vol. 85, no. 5, p. 1204. doi 10.1134/S1070363215050370

    Article  CAS  Google Scholar 

  13. Sheldrick, G.M., SADABS, Madison, USA Bruker AXS, 1997.

    Google Scholar 

  14. Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Crystallogr., Sect. A, 1991, vol. 47, p. 744. doi 10.1107/S0108767391006566

    Article  Google Scholar 

  15. Sheldrick, G.M., SHELX-97. Programs for Crystal Structure Analysis (Release 97-2), Göttingen: Univ. of Göttingen, 1997, vols. 1, 2.

    Google Scholar 

  16. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837. doi 10.1107/S0021889899006020

    Article  CAS  Google Scholar 

  17. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions, Madison, Wisconsin, US: Bruker AXS.

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Correspondence to M. A. Pudovik.

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Original Russian Text © M.A. Pudovik, S.A. Terent’eva, A.B. Dobrynin, R.Kh. Bagautdinova, L.K. Kibardina, E.M. Pudovik, A.R. Burilov, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 1, pp. 64–69.

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Pudovik, M.A., Terent’eva, S.A., Dobrynin, A.B. et al. 2-(2-Hydroxyphenyl)imidazolidines and their O-phosphorylated derivatives. Russ J Gen Chem 87, 60–65 (2017). https://doi.org/10.1134/S107036321701011X

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  • DOI: https://doi.org/10.1134/S107036321701011X

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