Advertisement

Russian Journal of Organic Chemistry

, Volume 41, Issue 12, pp 1757–1763 | Cite as

Synthesis of 4-Formyl-3-cyclopentene-1,1,2-tricarbonitriles

  • V. P. Sheverdov
  • O. V. Ershov
  • A. V. Eremkin
  • O. E. Nasakin
  • I. N. Bardasov
  • V. A. Tafeenko
Article

Abstract

β,β,γ,γ-Tetracyanoalkanones react with acrolein at a high rate to afford the corresponding 2-substituted 4-formyl-3-cyclopentene-1,1,2-tricarbonitriles in high yields. The reaction occurs under mild conditions and is quite applicable for modification of natural and biologically active compounds possessing an R′CHC(O)CR3 fragment to obtain their derivatives containing three cyano groups.

Keywords

Organic Chemistry Active Compound Mild Condition Cyano Acrolein 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    Nasakin, O.E., Lukin, P.M., Zil'berg, S.P., Terent'ev, P.B., Bulai, A.K., D'yachenko, O.A., Zolotoi, A.B., Konovalikhin, S.V., Gusev, A.I., Sheludyakov, V.D., and Atovmyan, L.O., Zh. Org. Khim., 1988, vol. 24, p. 1007.Google Scholar
  2. 2.
    Nasakin, O.E., Sheverdov, V.P., Lukin, P.M., Tafeenko, V.A., and Bulai, A.K., Zh. Org. Khim., 1992, vol. 28, p. 1841.Google Scholar
  3. 3.
    Nasakin, O.E., Lukin, P.M., Zil'berg, S.P., Terent'ev, P.B., Bulai, A.K., Zolotoi, A.B., Konovalikhin, S.V., and Atovmyan, L.O., Zh. Org. Khim., 1988, vol. 24, p. 997.Google Scholar
  4. 4.
    Nasakin, O.E., Sheverdov, V.P., Moiseeva, I.V., Ershov, O.V., Chernushkin, A.N., and Tafeenko, V.A., Russ. J. Gen. Chem., 1999, vol. 69, p. 291.Google Scholar
  5. 5.
    Shinya, N., Naoki, A., Takashi, and Toshino, I., Chem. Lett., 1991, p. 495.Google Scholar
  6. 6.
    Armesto, D., Ramos, A., Mayoral, E.P., Ortiz, M.J., and Agarrabeitia, A.R., Org. Lett., 2000, no. 2, p. 183.Google Scholar
  7. 7.
    Zolotoi, A.B., Sheverdov, V.P., Lukin, P.M., Prokhorov, A.I., Konovalikhin, S.V., Nasakin, O.E., and Atovmyan, L.O., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, p. 1442.Google Scholar
  8. 8.
    Sheverdov, V.P., Bulkin, V.V., Ershov, O.V., Nasakin, O.E., and Tafeenko, V.A., Russ. J. Gen. Chem., 2002, vol. 72, p. 909.Google Scholar
  9. 9.
    Dawson, R.M.C., Elliott, D.C., Elliott W.H., and Jones, K.M., Data for Biochemical Research, Oxford: Clarendon, 1986, 3rd ed.Google Scholar
  10. 10.
    Andrews, A.L., Fort, R.C., and Le Quesne, P.W., J. Org. Chem., 1971, vol. 36, p. 83.CrossRefGoogle Scholar
  11. 11.
    Diaba, F., Le Houerou, C., Grignon-Dubois, M., and Gerval, P., J. Org. Chem., 2000, vol. 65, p. 907.CrossRefGoogle Scholar
  12. 12.
    Griomi, D., Nesi, R., Turchi, S., and Mura, E., J. Org. Chem., 2000, vol. 65, p. 360.Google Scholar
  13. 13.
    Milddenton, W.J., Heckert, R.E., Little, E.L., and Krespan, C.G., J. Am. Chem. Soc., 1958, vol. 80, p. 2783.Google Scholar
  14. 14.
    Nasakin, O.E., Nikolaev, E.G., Terenfev, P.B., Khashin, B.A., and Petrov, V.G., Zh. Org. Khim., 1984, vol. 20, p. 205.Google Scholar
  15. 15.
    Nasakin, O.E., Nikolaev, E.G., Terent'ev, P.B., Bulai, A.Kh., Khashin, B.A., and Mikhailov, V.K., Khim. Geterotsikl. Soedin., 1984, p. 1574.Google Scholar
  16. 16.
    Nasakin, O.E., Nikolaev, E.G., Terent'ev, P.B., Bulai, A.Kh., and Zharkov, V.Ya., Khim. Geterotsikl. Soedin., 1985, p. 1225.Google Scholar
  17. 17.
    Nasakin, O.E., Nikolaev, E.G., Terent'ev, P.B., and Bulai, A.Kh., Khim. Geterotsikl. Soedin., 1987, p. 653.Google Scholar
  18. 18.
    Nasakin, O.E., Sheverdov, V.P., Moiseeva, I.V., Ershov, O.V., Lyshchikov, A.N., and Nesterov, V.N., Tetrahedron Lett., 1997, vol. 38, p. 4455.CrossRefGoogle Scholar
  19. 19.
    Nasakin, O.E., Sheverdov, V.P., Ershov, O.V., Moiseeva, I.V., Lyshchikov, A.N., Khrustalev, V.N., and Antipin, M.Yu., Mendeleev Commun., 1997, p. 112.Google Scholar
  20. 20.
    Nasakin, O.E., Nikolaev, E.G., Terenfev, P.B., Bulai, A.Kh., and Kalandarishvili, A.G., Khim. Geterotsikl. Soedin., 1985, p. 1027.Google Scholar
  21. 21.
    Allen, F.H., Acta Crystallogr., Sect. B, 2002, vol. 58, p. 380.Google Scholar
  22. 22.
    Sheldrick, G.M., SHELXS97 & SHELXL97, Gottingen: Univ. Gottingen, 1997.Google Scholar

Copyright information

© MAIK "Nauka/Interperiodica" 2005

Authors and Affiliations

  • V. P. Sheverdov
    • 1
  • O. V. Ershov
    • 1
  • A. V. Eremkin
    • 1
  • O. E. Nasakin
    • 1
  • I. N. Bardasov
    • 1
  • V. A. Tafeenko
    • 2
  1. 1.I.N. Ul'yanov Chuvash State UniversityCheboksaryRussia
  2. 2.Faculty of ChemistryMoscow State UniversityMoscowRussia

Personalised recommendations