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γ-Piperidone imines and enamies in organic synthesis (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The methods of preparation, structure, and some chemical conversions of imines and enamines based on γ-piperidones were examined.

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References

  1. A. G. N. Cook (ed.), Enamines: Synthesis, Structure, and Reactions, Marcel Dekker, New York (1969).

    Google Scholar 

  2. B. U. Minbaev, Schiff Bases [in Russian], Nauka, KazSSR, Alma-Ata (1989).

    Google Scholar 

  3. V. V. Kuznetsov and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 1, 5 (1990).

  4. R. S. Bartanyan, Khim. Farm. Zh., No. 5, 540 (1983).

  5. V. V. Kuznetsov, Khim. Farm. Zh., No. 7, 61 (1991).

  6. A. E. Aliev, V. V. Kuznetsov, L. A. Gaivoronskaya, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 10, 1405 (1989).

  7. N. S. Prostakov, A. A. Fomichev, N. I. Golovtsov, V. A. Rezakov, and A. V. Varlamov, Zh. Org. Khim.,24, 2313 (1988)

    Google Scholar 

  8. N. S. Prostakov, L. A. Gaivoronskaya, Sankar K. Das, and V. F. Zakharov. Izv. Vyssh. Uchebn. Zaved., Radioiz. Khim. Khim. Tekhnol.,24, 1490 (1981).

    Google Scholar 

  9. V. A. Rezakov, S. K. Das, A. A. Fomichev, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 10, 1367 (1986).

  10. V. I. Mikhailov, V. D. Sholle, E. Sh. Kogan, and E. T. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1639 (1976).

  11. M. Alam, J. D. Baty, G. Jones, and C. Moore, J. Chem. Soc. (C), No. 11, 1520 (1969).

  12. J. Barluenga, F. Aznar, M. P. Cabal, F. H. Cano, and C. Faces-Faces, J. Chem. Soc. Chem. Conimun., No. 18, 1247 (1988).

  13. J. Barluenga, F. Aznar, M. P. Cabal, and C. Valdes, J. Chem. Soc. Perkin Trans. 1, No. 3, 633 (1990).

  14. R. Huisgen and K. Herbig, Ann.,688, 98 (1965).

    Google Scholar 

  15. V. V. Kuznetsov, S. K. Das, L. A. Gaivoronskaya, V. F. Zakharov, and N. S. Prostakov, submitted to VINITI, No. 5036 (07.12,84); Ref. Zh. Khim., 22Zh225 (1984).

  16. V. V. Kuznetsov, E. E. Stashenko, L. A. Gaivoronskaya, and N. S. Prostakov, Submitted to ONIITEKhim, No. 714-khp (05.29.86)

  17. E. E. Stashenko, V. V. Kuznetsov, L. A. Gaivoronskaya, P. L Zakharov, and N. S. Prostakov, Submitted to VINITI, 6849 (09.25.86); Ref. Zh. Khim., 2BI129 (1987).

  18. V. V. Kuznetsov, L. A. Gaivoronskaya, L. A. Murgova, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 7, 943 (1986).

  19. E. L. Gaidarova, G. V. Grishina, V. M. Potapov, M. Yu. Kornilov, and M. V. Kozhinskaya, USSR Inventor's Certificate No, 1,384,579; Byull. Izobr., No. 12 (1988).

  20. G. V. Grishina, E. L. Gaidarova, and A. E. Aliev, Khim. Geterotsikl. Soedin., No. 10, 1369 (1992).

  21. G. V. Grishina. E. L. Gaidorova, and A. E. Aliev, in: Proceedings of the Vth All-Union Conference on the Chemistry of Nitrogen-Containing Heterocyclic Compounds [in Russian], Part 2, Chernogolovka (1991), p. 101.

  22. G. V. Grishina and E. L. Gaydarova, Synlett., No. 1, 64 (1992).

  23. M. F. Shostakovskii, B. U. Minbaev, and O. V. Agashkin, Dokl. Akad. Nauk,251, 1144 (1980).

    Google Scholar 

  24. V. V. Kuznetsov, 1. G. Mobio, K. Tapan, and A. Zh. Litvinov, in:Proceedings of the 9th Mol. Conf. on Synthetic and Natural Physiologically Active Compounds [in Russian], Erevan (1988), p. 3.

  25. T. K. Mandal, 1. G. Mobio, V. V. Kuznetsov, A. Zh. Litvinov, E. N. Denisov, V. 0. Fedorov, E. I. Andreeva, A. T. Soldatenkov, and N. S. Prostakov, Khim. Farm. Zh., No. 6, 28 (1991).

  26. V. V. Kuznetsov, Yu. 1. Naumov, L. 1. Minaev, E. 1. Andreeva, and N. S. Prostakov, Khim. Farm. Zh., No. 6, 24 (1991).

  27. R. Fusco, G. Bianchetti, and S. Rossi, Gaz. Chim. Ital.,91, 825 (1961).

    Google Scholar 

  28. J. Belsky, Tetrahedron Lett., No. 52, 4597 (1970).

  29. G. Cordonnier and H. Sliwa, J. Heterocycl. Chem.,24, 111 (1987).

    Google Scholar 

  30. S. G. Pilosyan, V. V. Dobaeva, B. D. Enokyan, E. A. Abgaryan, and A. S. Norovyan, Arm. Khim. Zh.,41. 687 (1988).

    Google Scholar 

  31. R. L. Augustine, J. Org. Chem.,23, 1853 (1958).

    Google Scholar 

  32. L. Birkofer, S. M. Kim, and H. D. Engels, Chem. Ber.,95, 1495 (1962).

    Google Scholar 

  33. S. Danishefsky and R. Cavanaugh, J. Org. Chem.,33, 2959 (1968).

    Google Scholar 

  34. K. C. Brannick, R. D. Burpitt, V. W. Goodlett, and J. G. Thweatt, J. Org. Chem.,29, 813 (1964).

    Google Scholar 

  35. M. Nakanishi, M. Yatabe, and M. Hamana, Heterocycles,3, 287 (1975).

    Google Scholar 

  36. M. Hamana and S. Saeki, J. Jap. Chem., No. 123, 219 (1979); Ref. Zh. Khim., 7Zh275 (1980).

  37. Japanese Patent No. 7,436,380; Chem. Abstr.,81, 91361 (1974).

    Google Scholar 

  38. K. D. Praliev, D. M. Manatausov, N. A. Belikova, D. V. Sokolov, V. M. Kurilenko, Zh. N. Klieriko, and L. M. Moiseeva, Khmi. Farm. Zh., No. 9, 58 (1980).

  39. R. S. Vartanyan, V. O. Martirosyan, E. V. Vlasenko, L. K. Durgaryan, and A. S. Azlivyan, Khim. Farm. Zh., No. 3, 43 (1981)

  40. N. S. Prostakov, A. A. Fomichev, L. A. Gaivoronskaya, N. I. Golovtsov, and S. K. Das, Khim. Geterotsikl. Soedin., No. 11, 1512 (1982).

  41. R. S. Vartanyan, V. O. Martirosyan, S. A. Vartanyan, E. V. Vlasenko, L. K. Durgaryan, and A. S. Azlivyan, Khim. Farm. Zh., No. 5, 562 (1989).

  42. R. S. Vartanyan, V. O. Martirosyan, L. V. Matevosyan, and S. A. Vartanyan, Arm. Khim. Zh.,40, No. 9, 593 (1987).

    Google Scholar 

  43. V. V. Kuznetsov, L. A. Gaivoronskaya, A. A. Fomichev, R. M. Romero, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 7, 949 (1987).

  44. A. A. Fomichev, R. M. Romero, N. I. Golovtsov, V. V. Kuznetsov, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 1, 54 (1988).

  45. A. A. Karapetyan, Yu. T. Struchkov, T. V. Timofeeva, V. O. Martirosyan, R. S. Vartanyan, and S. A. Vartanyan, Khim. Farm. Zh., No. 5, 565 (1989).

  46. L. A. Gaivoronskaya, T. A. Kapitonenko, S. K. Das, N. Z. Burdi, A. S. Zaks, and N. S. Prostakov, Khim. Farm. Zh., No. 9, 1076 (l984).

  47. E. E. Stashenko, P. 1. Zakharov, V. V. Kuznetsov, L. A. Gaivoronskaya, B. S. Subbotin, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 6, 813 (1988).

  48. R. S. Vartanyan, V. O. Martirosyan, S. A. Vartanyan, A. P. Enchoyan, E. V. Vlasenko, L. K. Durgaryan, A. S. Azlivyan, and A. V. Val'dman, Khim. Farm. Zh., No. 5, 573 (1989).

  49. USSR Inventor's Certificate No. 736,583; Byull. Izobr., No. 44 (1985).

  50. I. N. Nazarov, N. S. Prostakov, N. N. Mikheeva, and V. N. Dobrynin, Izv. Vyssh. Uchebn. Zaved., Radiofiz. Khim. Khim. Tekhnol.,11, 726 (1958).

    Google Scholar 

  51. V. V. Kuznetsov, L. A. Gaivoronskaya, R. M. Romero, E. E. Stashenko, P. I. Zakharov, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 7, 954 (1987).

  52. N. S. Prostakov, L. A. Gaivoronskaya, N. M. Mikhailova, and L. M. Kirillova, Zh. Obshch. Khim.,33, 2573 (1963).

    Google Scholar 

  53. N. S. Prostakov, V. V. Kuznetsov, and E. E. Stashenko, Khim. Geterotsiki. Soedin., No. 11, 1514 (1989).

  54. V. V. Kuznetsov, A. E. Aliev, S. V. Lantsetov, A. S. Dvuzhilov, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 7, 942 (1991).

  55. V. V. Kuznetsov and N. S. Prostakov, in:Proceedings of the 5th All-Union Symposium on Organic Synthesis [in Russian], Moscow (1988), p. 176.

  56. V. V. Kuznetsov, S. V. Lantsetov, A. E. Aliev, A. V. Varlamov, and N. S. Prostakov, in:Proceedings of the Vth All-Union Conference on the Chemistry of Nitrogen-Containing Heterocyclic Compounds [in Russian], Chernogolovka (1991), p. 237; Ref. Zh. Khim., 10Zh243 (1992).

  57. V. V. Kuznetsov, S. V. Lantsetov, A. E. Aliev, A. V. Varlamov, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 11, 1528 (1991).

  58. S. V. Lantsetov, V. V. Kuznetsov, L. A. Simeoni, N. S. Prostakov, and A. V. Varlamov, in: Proceedings of the 27th Scientific Conference of the Faculty of Physical-Mathematical and Natural Sciences, Russian People's Friendship University [in Russian], Moscow (1991), p. 187; Ref. Zh. Khim., 3Zh259 (1992).

  59. N. S. Prostakov, L. A. Shakhparonova, and L. M. Kirillova, Zh. Obshch. Khim.,34, 3231 (1964).

    Google Scholar 

  60. N. S. Prostakov, L. M. Kirillova, D. Pkhal'gumani, L. A. Shakhparonova, and V. P. Zvolinskii, Khim. Geterotsikl. Soedin., No. 8, 1068 (1967).

  61. N. S. Prostakov, V. G. Pleshakov, T. Kholdarova, V. P. Zvolinskii, and L. N. Plaksii, Khim. Geterotsikl. Soedin., No. 3, 378 (1972).

  62. N. S. Prostakov, V. G. Pleshakov, T. Kholdarova, V. P. Zvolinskii, and L. N. Plaksii, Khim. Geterotsikl. Soedin., No. 10, 1400 (1972).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–17, January, 1994.

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Kuznetsov, V.V., Prostakov, N.S. γ-Piperidone imines and enamies in organic synthesis (review). Chem Heterocycl Compd 30, 1–13 (1994). https://doi.org/10.1007/BF01164723

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