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Synthesis and spectroscopic investigation of the new polyfluoroalkyl-containing indazolones

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Abstract

Reaction of 2-perfluoroacylcycloalkane-1,3-diones and their enol methyl esters with N,N-dinucleophiles such as 4-fluorophenylhydrazine hydrochloride and pentafluorophenylhydrazine results in formation of polyfluoroalkyl-containing 1-aryl-3-polyfluoroalkyl-6,7-dihydro-1H-indazol-4(5)H-ones and 2-aryl-3-polyfluoroalkyl-6,7-dihydro-2H-indazol-4(5)H-ones respectively. Structure of compounds obtained was proved with IR, 1H, 13C, 19F, 15N NMR, and mass-spectrometric methods.

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References

  1. Cerecetto, H., Gerpe, A., González, M., Arán, V.J., and de Ocárizi, C.O., Mini-Reviews in Medicinal Chemistry, 2005, vol. 5, no. 10, p. 869.

    Article  CAS  Google Scholar 

  2. El-Hawash, S.A.M., Badawey, El-S.A.M., and El-Ashmawey, I.M., Eur. J. Med. Chem., 2006, vol. 41, no. 2, p. 155.

    Article  CAS  Google Scholar 

  3. Xu, W., Huang, L.-F., Bauer, L., Bhargava, H.N., and Dunn, W.J., Bioorg. Med. Chem. Lett., 1999, vol. 9, no. 23, p. 3375.

    Article  CAS  Google Scholar 

  4. Lorand, T., Kocsis, B., Emody, L., and Sohar, P., Eur. J. Med. Chem., 1999, vol. 34, no. 11, p. 1009.

    Article  CAS  Google Scholar 

  5. Kirsch, P., Modern Fluoroorganic Chemistry, Weinheim: WILEY-VCH Verlag GmbH, 2004, p. 299.

    Book  Google Scholar 

  6. Jeschke, P., Chem. Bio. Chem., 2004, vol. 5, no. 7, p. 571.

    Google Scholar 

  7. Furin, G.G., Khim. Geterotsykl. Soedin., 2006, no. 3. p. 323.

  8. Piccionello, A.P., Pace, A., Pibiri, I., Buscemi, S., and Vivona, N., Tetrahedron, 2006, vol. 62, no. 37, p. 8792.

    Article  Google Scholar 

  9. Pryadeina, M.V., Burgart, Ya.V., Kodess, M.I., Saloutin, V.I., and Chupakhin, O.N., Izv. Akad. Nauk, Ser. Khim., 2004, no. 6, p. 1210.

  10. Sloop, J.C., Bumgardner, C.L., and Loehle, W.D., J. Fluorine Chem., 2002, vol. 118, no. 2, p. 135.

    Article  CAS  Google Scholar 

  11. Kumar, V., Aggarwal, R., and Singh, S.P., J. Fluorine Chem., 2006, vol. 127, no. 7, p. 880.

    Article  CAS  Google Scholar 

  12. Sevenard, D.V., Khomutov, O.G., Kodess, M.I., Pashkevich, K.I., Loop, I., Lork, E., and Röschenthaler, G.-V., Canad. J. Chem., 2001, vol. 79, no. 2, p. 183.

    Article  CAS  Google Scholar 

  13. Saloutin, V.I., Burgart, Ya.V., and Chupakhin, O.N. Ftorosoderzhashchie trikarbonil’nye soedinenia (Fluoro-Containing Tricarbonyl Compounds), Yekaterinburg, 2002, p. 242.

  14. Rubinov, D.B., Rubinova, I.L., and Akhrem, A.A., Chem. Rev., 1999, vol. 99, no. 4, p. 1047.

    Article  CAS  Google Scholar 

  15. Khlebnikova, T.S., Zinovich, V.G., and Lakhvich, F.A., Dokl. Nats. Akad. Nauk Bel., 2005, vol. 49, no. 5, p. 68.

    CAS  Google Scholar 

  16. Khlebnikova, T.S., Isakova, V.G., Baranovsky, A.V., Borisov, E.V., and Lakhvich F.A., J. Fluorine Chem., 2006, vol. 127, no. 12, p. 1564.

    Article  Google Scholar 

  17. Akhrem, A.A., Moiseenkov, A.M., Lakhvich, F.A., and Krivoruchko, V.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1969, no. 9, p. 2013.

  18. Lakhvich, F.A., Lis, L.G., Rubinov, D.B., and Borisov, E.V., Zh. Org. Khim., 1988, vol. 24, no. 4, p. 755.

    CAS  Google Scholar 

  19. Strakova, I.A., Strakov, A.Ya., Strautzele, M.T., and Gudrinietse, E.Yu., Izv. Akad. Nauk Latv. SSR, Ser. Khim., 1968, no. 5, p. 597.

  20. Strakova, I.A., Strakov, A.Ya., and Petrova, M.V., Khim. Geterotsykl. Soedin., 2002, no. 4, p. 494.

  21. Akhrem, A.A., Moiseenkov, A.M., and Andaburskaya, M.B., Izv. Akad. Nauk SSSR, Ser. Khim., 1969, no. 12, p. 2846.

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Correspondence to T. S. Khlebnikova.

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Original Russian Text © T.S. Khlebnikova, V.G. Isakova, A.V. Baranovskii, F.A. Lakhvich, 2008, published in Zhurnal Obshchei Khimii, 2008, vol. 78, No. 10, pp. 1718–1727.

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Khlebnikova, T.S., Isakova, V.G., Baranovskii, A.V. et al. Synthesis and spectroscopic investigation of the new polyfluoroalkyl-containing indazolones. Russ J Gen Chem 78, 1954–1963 (2008). https://doi.org/10.1134/S1070363208100241

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  • DOI: https://doi.org/10.1134/S1070363208100241

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