Russian Journal of Organic Chemistry

, Volume 48, Issue 6, pp 860–863 | Cite as

Synthesis of Schiff bases from 3-amino-3-arylpropionic acid esters in aqueous medium

  • N. N. Romanova
  • I. I. Rybalko
  • T. G. Tallo
  • N. V. Zyk
  • V. K. Švedas
Short Communications
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References

  1. 1.
    Mahmood-Ul-Hassan, Chohan, Z.H., Scozzafava, A., and Supuran, C.T., J. Enzyme Inhib. Med. Chem., 2004, vol. 19, p. 263; Puccetti, L., Fasolis, G., Vullo, D., Chohan, Z.H., Scozzafava, A., and Supuran, C.T., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 3096.CrossRefGoogle Scholar
  2. 2.
    Hewett-Emmett, D., The Carbonic Anhydrases: New Horizons, Chegwidden, W.R., Carter, N.D., and Edwards, Y.H., Eds., Basel: Birkhäuser, 2000, p. 29; Supuran, C.T. and Scozzafava, A., Expert Opin. Ther. Pat., 2000, vol. 10, p. 575.Google Scholar
  3. 3.
    Renard, J.P., Giraud, J.M., and Oubaaz, A., J. Fr. Ophthalmol., 2004, vol. 27, p. 701.CrossRefGoogle Scholar
  4. 4.
    Supuran, C.T., Expert Opin. Ther. Pat., 2003, vol. 13, p. 1545.CrossRefGoogle Scholar
  5. 5.
    Supuran, C.T., Vullo, D., Manole, G., Casini, A., and Scozzafava, A., Curr. Med. Chem. Cardiovasc. Hematol. Agents, 2004, vol. 2, p. 49.CrossRefGoogle Scholar
  6. 6.
    Robertson, N., Potter, C., and Harris, A.L., Cancer Res., 2004, vol. 64, p. 6160.CrossRefGoogle Scholar
  7. 7.
    Epstein, D.L. and Grant, W.M., Arch. Ophthalmol., 1977, vol. 95, no. 8, p. 1378.CrossRefGoogle Scholar
  8. 8.
    Nasr, G., Petit, E., Supuran, C.T., Winum, J.-Y., and Barboiu, M., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 6014.CrossRefGoogle Scholar
  9. 9.
    El-Masry, A.N., Fahmy, H.H., and Abdelwahed, S.H.A., Molecules, 2000, vol. 21, p. 1429.CrossRefGoogle Scholar
  10. 10.
    Baseer, M.A., Jadhav, V.D., Phule, R.M., Archana, Y.V., and Vibhute, Y.B., Orient. J. Chem., 2000, vol. 16, no. 3, p. 553.Google Scholar
  11. 11.
    Hfndeya, S.N., Sriram, D., Nath, G., and De Clercq, E., Il Farmaco, 1999, vol. 54, p. 624.CrossRefGoogle Scholar
  12. 12.
    Singh, W.M. and Dash, B.C., Pesticides, 1988, vol. 22, no. 11, p. 33.Google Scholar
  13. 13.
    Samadhiya, S. and Halve, A., Orient. J. Chem., 2001, vol. 17, no. 1, p. 119.Google Scholar
  14. 14.
    Desai, S.B., Desai, P.B., and Desai, K.R., Heterocycl. Commun., 2001, vol. 7, no. 1, p. 83.CrossRefGoogle Scholar
  15. 15.
    Hodnett, E.M. and Dunn, W.J., J. Med. Chem., 1970, vol. 13, no. 4, p. 768.CrossRefGoogle Scholar
  16. 16.
    Staudinger, H., Ber., 1907, vol. 40, p. 1145; Staudinger, H., Justus Liebigs Ann. Chem., 1907, vol. 356, p. 51.Google Scholar
  17. 17.
    Liu, Z.-Y., Wang, Y.-M., Li, Z.-R., Jiang, J.-D., and Boykin, D.W., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 5661.CrossRefGoogle Scholar
  18. 18.
    Todorov, A.R., Kurteva, V.B., Bontchev, R.P., and Vassilev, N.G., Tetrahedron, 2009, vol. 65, p. 10339.CrossRefGoogle Scholar
  19. 19.
    Bhalla, A., Venugopalan, P., and Bari, S.S., Tetrahedron, 2006, vol. 62, p. 8291; Fu, N. and Tidwell, T.T., Tetrahedron, 2008, vol. 64, p. 10 465; Cheemala, M.N. and Knochel, P., Org. Lett., 2007, vol. 9, p. 3089; Bari, S.S., Reshma, Bhalla, A., and Hundal, G., Tetrahedron, 2009, vol. 65, p. 10 060; Hu, L., Wang, Y., Li, B., Du, D.-M., and Xu, J., Tetrahedron, 2007, vol. 63, p. 9387.CrossRefGoogle Scholar
  20. 20.
    Shang, G., Yang, Q., and Zhang, X., Angew. Chem., Int. Ed., 2006, vol. 45, p. 6360; Ross, N.A., Mac-Gregor, R.R., and Bartsch, R.A., Tetrahedron, 2004, vol. 60, p. 2035; Joffe, A.L., Thomas, T.M., and Adrian, J.C., Jr., Tetrahedron Lett., 2004, vol. 45, p. 5087; Veverkova, E., Strasserova, J., Sebesta, R., and Toma, S., Tetrahedron: Asymmetry, 2010, vol. 21, p. 58; Zhang, H., Syed, S., and Barbas, C.F. III, Org. Lett., 2010, vol. 12, p. 708.CrossRefGoogle Scholar
  21. 21.
    Soengas, R.G., Segad, J., Jimenez, C., and Rodriguez, J., Tetrahedron, 2011, vol. 67, p. 2617.CrossRefGoogle Scholar
  22. 22.
    Choudhury, L.H. and Parvin, T., Tetrahedron, 2011, vol. 67, p. 8213.CrossRefGoogle Scholar
  23. 23.
    Soloshonok, V.A., Fokina, N.A., Rybakova, A.V., Shishkina, I.P., Galushko, S.V., Sorochinsky, A.E., Kukhar, V.P., Savchenko, M.V., and Švedas, V.K., Tetrahedron: Asymmetry, 1995, vol. 6, p. 1601.CrossRefGoogle Scholar
  24. 24.
    Soloshonok, V.A., Švedas, V.K., Kukhar, V.P., Kirilenko, A.G., Galaev, I.Yu., Kozlova, E.V., Shishkina, I.P., and Galushko, S.V., Synlett, 1993, p. 339; Romanova, N.N., Gravis, A.G., Kudan, P.V., and Bundel’, Ju.G., Mendeleev Commun., 2001, no. 1, p. 26; Romanova, N.N., Gravis, A.G., Kudan, P.V., Leshcheva, I.F., and Zyk, N.V., Russ. J. Org. Chem., 2003, vol. 39, p. 692; Romanova, N.N., Tallo, T.G., Rybalko, I.I., Zyk, N.V., and Shvyadas, V.K., Chem. Heterocycl. Compd., 2011, no. 4, p. 395.Google Scholar
  25. 25.
    Adriaenssens, L.V. and Hartley, R.C., J. Org. Chem., 2007, vol. 72, p. 10 287.CrossRefGoogle Scholar
  26. 26.
    Mokhallalati, M.K. and Pridgen, L.N., Synth. Commun., 1993, vol. 23, no. 14, p. 2055.CrossRefGoogle Scholar
  27. 27.
    Schiff, H., Justus Liebigs Ann. Chem., 1864, vol. 131, p. 118.CrossRefGoogle Scholar
  28. 28.
    Taguchi, K. and Westheimer, F.H., J. Org. Chem., 1971, vol. 36, p. 1570.CrossRefGoogle Scholar
  29. 29.
    Hania, M.M., E-J. Chem., 2009, vol. 6, no. 3, p. 629. doi 10.1155/2009/104058CrossRefGoogle Scholar
  30. 30.
    Guzen, K.P., Guarezemini, A.S., Orfao, A.T.G., Cella, R., Pereira, C.M.P., and Stefani, H.A., Tetrahedron Lett., 2007, vol. 48, p. 1845.CrossRefGoogle Scholar
  31. 31.
    Caddick, S.R., Tetrahedron, 1995, vol. 51, p. 10 403; Lidstrom, P., Tierney, J., Wathey, B., and Westman, J., Tetrahedron, 2001, vol. 57, p. 9225; Romanova, N.N., Gravis, A.G., and Zyk, N.V., Usp. Khim., 2005, vol. 74, p. 1059; Caddick, S. and Fitzmaurice, R., Tetrahedron, 2009, vol. 65, p. 3325.CrossRefGoogle Scholar
  32. 32.
    Varma, R.S., Dahiya, R., and Kumar, S., Tetrahedron Lett., 1997, vol. 38, p. 2039.CrossRefGoogle Scholar
  33. 33.
    Godoy-Alcantar, C., Yatsimirsky, A.K., and Lehn, J.-M., J. Phys. Org. Chem., 2005, vol. 18, p. 979.CrossRefGoogle Scholar
  34. 34.
    Simon, A., Simon, C., Kanda, T., Nagashima, S., Mitoma, Y., Yamada, T., Mimura, K., and Tashiro, M., J. Chem. Soc., Perkin. Trans. 1, 2001, p. 2071.Google Scholar
  35. 35.
    Saggiomo, V. and Luning, U., Tetrahedron Lett., 2009, vol. 50, p. 4663.CrossRefGoogle Scholar
  36. 36.
    Rodionow, W.M. and Postovskaja, E.A., J. Am. Chem. Soc., 1929, vol. 51, p. 841; Rodionow, W.M., J. Am. Chem. Soc., 1929, vol. 51, p. 847.CrossRefGoogle Scholar
  37. 37.
    Tan, C.Y.K. and Weaver, D.F., Tetrahedron, 2002, vol. 58, p. 7449.CrossRefGoogle Scholar
  38. 38.
    Nejman, M., Sliwinska, A., and Zwierzak, A., Tetrahedron, 2005, vol. 61, p. 853.CrossRefGoogle Scholar
  39. 39.
    Tasnadi, G., Forro, E., and Fulop, F., Tetrahedron: Asymmetry, 2008, vol. 19, p. 2072.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • N. N. Romanova
    • 1
  • I. I. Rybalko
    • 1
  • T. G. Tallo
    • 2
  • N. V. Zyk
    • 1
  • V. K. Švedas
    • 3
  1. 1.Faculty of ChemistryMoscow State UniversityMoscowRussia
  2. 2.National Institute for Health DevelopmentTallinnEstonia
  3. 3.Belozerskii Institute of Physicochemical BiologyMoscow State UniversityMoscowRussia

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