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Synthesis of 5-oxoalkane-2,2,3,3-tetracarbonitriles

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Abstract

5-Oxoalkane-2,2,3,3-tetracarbonitriles have been synthesized by reaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with methyl iodide in dimethyl sulfoxide.

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References

  1. Nasakin, O.E., Lyshchikov, A.N., Pavlov, V.V., Shishkin, O.V., Nesterov, V.N., Khrustalev, V.N., Antipin, M.Yu., and Urman, Ya.G., Russ. J. Org. Chem., 1999, vol. 35, no. 9, p. 1337.

    CAS  Google Scholar 

  2. Ershov, O.V. Lipin, K.V., Maksimova, V.N., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2009, vol. 45, no. 3, p. 475.

    Article  CAS  Google Scholar 

  3. Belikov, M.Yu., Ershov, O.V., Lipovskaya, I.V., Nasakin, O.E., Sattarova, L.F., Strunin, B.P., Antipov, V.A., and Gurevich, P.A., Vestn. Kazan. Tekhnol. Univ., 2010, no. 9, p. 112.

    Google Scholar 

  4. Belikov, M.Yu. Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Gen. Chem., 2010, vol. 80, no. 10, p. 2078.

    Article  CAS  Google Scholar 

  5. Belikov, M.Yu., Ershov, O.V., Lipovskaya, I.V., Eremkin, A.V., and Nasakin, O.E., Russ. J. Org. Chem., 2011, vol. 47, no. 9, p. 1426.

    Article  CAS  Google Scholar 

  6. Belikov, M.Yu., Ershov, O.V., Eremkin, A.V., Nasakin, O.E., Tafeenko, V.A., and Nurieva, E.V., Tetrahedron Lett., 2011, vol. 52, p. 6407.

    Article  CAS  Google Scholar 

  7. Gurevich, P.A., Fedoseev, S.V., Lipin, K.V., Ershov, O.V., Eremkin, A.V., Sattarova, L.F., and Nasakin, O.E., Vestn. Kazan. Tekhnol. Univ., 2012, vol. 15, no. 15, p. 59.

    Google Scholar 

  8. Fedoseev, S.V., Ershov, O.V., Belikov, M.Yu., Lipin, K.V., Bardasov, I.N., Nasakin, O.E., and Tafeenko, V.A., Tetrahedron Lett., 2013, vol. 54, p. 2143.

    Article  CAS  Google Scholar 

  9. Nikolaev, E.G., Cand. Sci. (Chem.) Dissertation, Moscow, 1985.

    Google Scholar 

  10. Carlucci, L., Ciani, G., Proserpio, D.M., and Sironi, A., Angew. Chem., Int. Ed. Engl., 1996, vol. 35, p. 1088.

    Article  CAS  Google Scholar 

  11. Belikov, M.Yu., Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2010, vol. 46, no. 4, p. 597.

    Article  CAS  Google Scholar 

  12. Hayotsyan, S.S., Mkryan, G.G., Aghekyan, A.A., and Melikyan, G.S., Heterocycl. Commun., 2012, vol. 4, p. 189.

    Google Scholar 

  13. Langhals, E. and Langhals, H., Tetrahedron Lett., 1990, vol. 31, no. 6, p. 859.

    Article  CAS  Google Scholar 

  14. Toyota, K., Kawasaki, S., and Yoshifuji, M., J. Org. Chem., 2004, vol. 69, no. 15, p. 5065.

    Article  CAS  Google Scholar 

  15. Chang, T.T., More, Sh.V., Lu, I.-H., Hsu, J.-C., Chen, T.-J., Jen, Ya.Ch., Lu, Ch.-K., and Li, W.-Sh., Eur. J. Med. Chem., 2011, vol. 46, p. 3810.

    Article  CAS  Google Scholar 

  16. Tanaka, M., Imai, M., Fujio, M., Sakamoto, E., Takahashi, M., Eto-Kato, Ya., Wu, X.M., Funakoshi, K., Sakai, K., and Suemune, H., J. Org. Chem., 2000, vol. 65, no. 18, p. 5806.

    Article  CAS  Google Scholar 

  17. Erfle, S., Rahn, T., Bendrath, F., Baumann, W., Michalik, D., Jiao, H., Spannenberg, A., Borner, A., and Langer, P., Tetrahedron, 2011, vol. 67, p. 8780.

    Article  CAS  Google Scholar 

  18. Chen, B.-Ch. and Lue, P., Org. Prep. Proced. Int., 1992, vol. 24, no. 2, p. 185.

    Article  CAS  Google Scholar 

  19. Bhirud, Sh.B., Johar, P.S., Sharma, E., Jamshad, D., and Prajapaty, R., Int. Patent no. WO2011/80756 A1, 2011.

    Google Scholar 

  20. Makosza, M. and Chesnokov, A., Tetrahedron, 2008, vol. 64, no. 25, p. 5925.

    Article  CAS  Google Scholar 

  21. Huang, Q., Richardson, P.F., Sach, N.W., Zhu, J., Liu, K.K.-C., Smith, G.L., and Bowles, D.M., Org. Process Res. Dev., 2011, no. 3, p. 556.

    Article  Google Scholar 

  22. Jiang, Y., Wu, N., Wu, H., and He, M., Synlett, 2005, no. 18, p. 2731.

    Article  Google Scholar 

  23. Deng, T. and Cai, Ch., J. Fluorine Chem., 2013, vol. 156, p. 183.

    Article  CAS  Google Scholar 

  24. Kumar, P., Li, P., Korboukh, I., Wang, T.L., Yennawar, H., and Weinreb, S.M., J. Org. Chem., 2011, vol. 76, no. 7, p. 2094.

    Article  CAS  Google Scholar 

  25. Kende, A.S., Koch, K., and Smith, C.A., J. Am. Chem. Soc., 1988, vol. 110, p. 2210.

    Article  CAS  Google Scholar 

  26. Bloomfield, J.J., J. Org. Chem., 1961, vol. 26, p. 4112.

    Article  CAS  Google Scholar 

  27. Sheldrick, G.M., Acta Crystallog., Sect. A, 2008, vol. 64, p. 112.

    Article  CAS  Google Scholar 

  28. Brandenburg, K. DIAMOND, Release 2.1d; Crystal Impact: Bonn, Germany, 2000.

    Google Scholar 

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, Moskovskii pr. 15, Cheboksary, 428015, Russia

    S. V. Fedoseev, O. V. Ershov, M. Yu. Belikov, O. E. Nasakin & V. P. Sheverdov

  2. Faculty of Chemistry, Moscow State University, Leninskie gory 1, Moscow, 119991, Russia

    V. A. Tafeenko

Authors
  1. S. V. Fedoseev
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  2. O. V. Ershov
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  3. M. Yu. Belikov
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  4. V. A. Tafeenko
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  5. O. E. Nasakin
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  6. V. P. Sheverdov
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Corresponding author

Correspondence to S. V. Fedoseev.

Additional information

Original Russian Text © S.V. Fedoseev, O.V. Ershov, M.Yu. Belikov, V.A. Tafeenko, O.E. Nasakin, V.P. Sheverdov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 7, pp. 957–959.

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Fedoseev, S.V., Ershov, O.V., Belikov, M.Y. et al. Synthesis of 5-oxoalkane-2,2,3,3-tetracarbonitriles. Russ J Org Chem 51, 936–939 (2015). https://doi.org/10.1134/S1070428015070076

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  • DOI: https://doi.org/10.1134/S1070428015070076

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