Advertisement

Chemistry of Heterocyclic Compounds

, Volume 16, Issue 2, pp 99–113 | Cite as

Synthesis of heterocyclic compounds in the presence of transition metal complexes (review)

  • G. A. Tolstikov
  • U. M. Dzhemilev
Article

Abstract

The most recent data on reactions involving the formation of heterocycles that take place in the presence of palladium, nickel, cobalt, and iron complexes are examined. The mechanisms of the reactions are discussed in the light of modern concepts of catalysis by metal complexes. The particular significance of metal complex catalysts for the synthesis of heterocycles with unique structures is demonstrated.

Keywords

Iron Nickel Cobalt Organic Chemistry Catalysis 
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.

Literature cited

  1. 1.
    A. Kashara, T. Isumi, K. Sato, M. Maemura, and T. Hayasaka, Bull. Chem. Soc. Jpn.,50, 1899 (1977).Google Scholar
  2. 2.
    D. Korte, L. Hegedus, and R. Wirth, J. Org. Chem.,42, 1329 (1977).CrossRefGoogle Scholar
  3. 3.
    T. Hosokawa, K. Maeda, and J. Moritani, Tetrahedron Lett., No. 10, 739 (1973).CrossRefGoogle Scholar
  4. 4.
    T. Hosokawa, H. Ohkata, and J. Moritani, Bull. Chem. Soc. Jpn.,48, 1533 (1975).Google Scholar
  5. 5.
    I. I. Moiseev, π Complexes in Liquid-Phase Oxidation [in Russian], Nauka, Moscow (1970).Google Scholar
  6. 6.
    P. Maitlis, The Organic Chemistry of Palladium, Vol. 2, Academic Press, New York (1971), p. 76.Google Scholar
  7. 7.
    A. Kasahara, T. Izmui, and M. Ooshima, Bull. Chem. Soc. Jpn.,47, 2526 (1974).Google Scholar
  8. 8.
    L. Nahum, J. Org. Chem.,33, 3601 (1968).CrossRefGoogle Scholar
  9. 9.
    Y. Falbe, H. Huppes, and F. Korte, Chem. Ber.,97, 1104 (1964).Google Scholar
  10. 10.
    J. Falbe, Carbon. Monoxide in Organic Synthesis, Springer-Verlag (1970).Google Scholar
  11. 11.
    A. N. Nesmeyanov (ed.), Organic Syntheses through Metal Carbonyls [in Russian], Mir, Moscow (1970).Google Scholar
  12. 12.
    J. Wender and P. Pino (eds.), Organic Synthesis through Metal Carbonyls, Vol. 2, Wiley, New York-London (1977).Google Scholar
  13. 13.
    C. Bird, J. Organometal. Chem.,47, 281 (1973).CrossRefGoogle Scholar
  14. 14.
    E. Schmitz, A. Striegler, R. Urban, and G. Zimmermann, East German Patent No. 96943 (1973); Ref. Zh. Khim., 18N113P (1975).Google Scholar
  15. 15.
    E. Schmitz, R. Urban, U. Heuck, G. Zimmermann, and E. Gründemann, J. Prakt. Chem.,318, 185 (1976).CrossRefGoogle Scholar
  16. 16.
    R. Lugo, Aspects of Homogeneous Catalysis: A Series of Advances, Reidel Publishing (1970).Google Scholar
  17. 17.
    K. Maeda, T. Hosokawa, Sh.-Y Marahashi, and Y. Moritani, Tetrahedron Lett., No. 51, 5075 (1973).CrossRefGoogle Scholar
  18. 18.
    T. Hosokawa, N. Shimo, K. Maeda, A. Sonoda, and Sh.-Y. Maruhashi, Tetrahedron Lett., No. 5, 383 (1976).CrossRefGoogle Scholar
  19. 19.
    L. Hegedus, G. Allen, and E. Waterman, J. Am. Chem. Soc.,98, 2674 (1976).CrossRefGoogle Scholar
  20. 20.
    M. Mori and J. Ban, Tetrahedron Lett., No. 21, 1803 (1976).CrossRefGoogle Scholar
  21. 21.
    B. Bogdanovic, P. Heimbach, M. Kröner, and G. Wilke, Ann.,727, 143 (1969).Google Scholar
  22. 22.
    M. Mori and J. Ban, Tetrahedron Lett., No. 21, 1807 (1976).CrossRefGoogle Scholar
  23. 23.
    M. Mori, K. Chiba, and J. Ban, Tetrahedron Lett., No. 12, 1037 (1977).CrossRefGoogle Scholar
  24. 24.
    H. Yoshimoto and H. Itatani, Bull. Chem. Soc. Jpn.,46, 2490 (1973).Google Scholar
  25. 25.
    B. Akermark, L. Eberson, E. Jonnsson, and E. Pattersson, J. Org. Chem.,40, 1365 (1975).CrossRefGoogle Scholar
  26. 26.
    B. Trost and J. Genet, J. Am. Chem. Soc.,98, 8516 (1976).CrossRefGoogle Scholar
  27. 27.
    B. Trost, Tetrahedron,33, 2615 (1977).CrossRefGoogle Scholar
  28. 28.
    P. Heimbach, P. Jolly, and G. Wilke, Adv. Organometal. Chem.,8, 1970.Google Scholar
  29. 29.
    P. Jolly and G. Wilke, The Organic Chemistry of Nickel, Academic Press, New York (1974).Google Scholar
  30. 30.
    P. Maitlis, The Organic Chemistry of Palladium, Vol. 1, Academic Press, New York (1971).Google Scholar
  31. 31.
    P. Heynes, Tetrahedron Lett., No. 42, 3687 (1970).CrossRefGoogle Scholar
  32. 32.
    R. Manyik, W. Walker, K. Atkins, and E. Hammack, Tetrahedron Lett., No. 43, 3813 (1970).CrossRefGoogle Scholar
  33. 33.
    A. De Smet and M. Anteunis, Org. Magn. Res.,5, 589 (1973).CrossRefGoogle Scholar
  34. 34.
    K. Ohno, T. Mitsuyasu, and J. Tsuji, Tetrahedron Lett., No. 1, 67 (1971).CrossRefGoogle Scholar
  35. 35.
    K. Ohno, T. Mitsuyasu, and J. Tsuji, Tetrahedron,28, 3705 (1972).CrossRefGoogle Scholar
  36. 36.
    Tsumura Ryuitiro and Madzaki Takaaki, Japanese Patent No. 1291 (1969); Ref. Zh. Khim., 15N136P (1972).Google Scholar
  37. 37.
    W. Friedrichsen and O. Goehre, US Patent No. 3576011 (1968); Ref. Zh. Khim., 4N22P (1971).Google Scholar
  38. 38.
    H. Watanabe, K. Maiudzaki, R. Tsumura, and T. Madzaki, Japanese Patent No. 48-6463 (1973); Ref. Zh. Khim., 24N171P (1973).Google Scholar
  39. 39.
    K. Ohno and J. Tsuji, Chem. Commun., No. 6, 247 (1971).Google Scholar
  40. 40.
    J. Kiji, K. Yamamoto, H. Tomita, and J. Furukawa, Chem. Commun., No. 13, 506 (1974).Google Scholar
  41. 41.
    G. A. Tolstikov, U. M. Dzhemilev, F. A. Selimov, I. Kh. Aminev, and E. M. Vyrypsev, Zh. Org. Khim.,13, 885 (1977).Google Scholar
  42. 42.
    U. M. Czhemilev, F. A. Selimov, E. G. Galkin, and G. A. Tolstikov, Izv. Akad. Nauk, SSSR, Ser. Khim., No. 6, 1359 (1977).Google Scholar
  43. 43.
    U. M. Dzhemilev, Doctoral Dissertation, Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow (1978).Google Scholar
  44. 44.
    U. M. Dzhemilev, L. Yu. Gubaidullin, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1469 (1978).Google Scholar
  45. 45.
    H. Peter and D. Reinehr, Helv. Chim. Acta,61, 1115 (1978).CrossRefGoogle Scholar
  46. 46.
    D. Reinehr, Helv. Chim. Acta,61, 1122 (1978).CrossRefGoogle Scholar
  47. 47.
    P. Heimbach, B. Hugelin, H. Peter, A. Kolott, and E. Troxler, Angew. Chem.,88, 29 (1976).Google Scholar
  48. 48.
    A. Kolott, Dissertation, Ruhr Universität, Bochum (1976).Google Scholar
  49. 49.
    L. Yu. Gubaidullin, Master's Dissertation, Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa (1979).Google Scholar
  50. 50.
    G. A. Tolstikov, U. M. Dzhemilev, L. Yu. Gubaidullin, and I. Kh. Aminev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2151 (1974).Google Scholar
  51. 51.
    G. A. Tolstikov, U. M. Dzhemilev, and L. Yu. Gubaidullin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1609 (1976).Google Scholar
  52. 52.
    G. A. Tolstikov, U. M. Dzhemilev, and L. Yu. Gubaidullin, Zh. Org. Khim.,12, 1645 (1976).Google Scholar
  53. 53.
    U. M. Dzhemilev, L. Yu. Gubaidullin, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1469 (1978).Google Scholar
  54. 54.
    U. M. Dzhemilev, G. A. Tolstikov, L. Yu. Gubaidullin, R. V. Kunakova, and F. A. Selimov, Material from the Fifth All-Union Conference on Catalytic Reactions in the Liquid Phase, Alma Ata [in Russian], Vol. 4 (1978), p. 97.Google Scholar
  55. 55.
    R. Backer and M. Nobbs, Tetrahedron Lett., No. 42, 3759 (1977).CrossRefGoogle Scholar
  56. 56.
    P. Heimbach, Angew, Chem., Int. Ed.,12, 975 (1973).CrossRefGoogle Scholar
  57. 57.
    R. Meyer, Dissertation, Ruhr Universität, Bochum (1973).Google Scholar
  58. 58.
    U. M. Dzhemilev, R. V. Kinakova, F. V. Sharipova, L. V. Spirikhin, L. M. Khalilov, E. V. Vasil'eva, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 600 (1979).Google Scholar
  59. 59.
    F. V. Sharipova, and R. V. Kunakova, Summaries of Papers Presented by Young Scientists [in Russian], Bashkir Branch, Academy of Sciences of the USSR, Ufa (1979), p. 21.Google Scholar
  60. 60.
    G. A. Tolstikov, U. M. Dzhemilev, R. V. Kunakova, F. Ya. Kanzafarov, Yu. A. Sangalov, and F. V. Sharipova, in: Catalytic Synthesis of Organic Sulfur Compounds [in Russian], Institute of Catalysis, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk (1979), p. 15.Google Scholar
  61. 61.
    H. Sukurai., J. Kamiyama, and N. Jasahira, Chem. Lett., No. 8, 887 (1975).Google Scholar
  62. 62.
    W. Hafner, H. Prigge, and J. Smidt, Ann.,693, 109 (1966).Google Scholar
  63. 63.
    J. Watkasuki and H. Jamazaki, Tetrahedron Lett., No. 36, 3383 (1973).CrossRefGoogle Scholar
  64. 64.
    H. Bönnemann, R. Brinkmann, and H. Benkluhn, Synthesis, No. 8, 575 (1974).CrossRefGoogle Scholar
  65. 65.
    H. Bönnemann and R. Brinkmann, Synthesis, No. 9, 600 (1975).CrossRefGoogle Scholar
  66. 66.
    H. Bönnemann, Angew. Chem.,90, 517 (1978).Google Scholar
  67. 67.
    J. Kusinoki and H. Okazaki, Hydrocarbon Process, No. 11, 129 (1974).Google Scholar
  68. 68.
    R. Noyori, J. Baba, S. Makino, and H. Takaya, Tetrahedron Lett., No. 20, 1741 (1973).CrossRefGoogle Scholar
  69. 69.
    H. Takaya, J. Hakagawa, S. Makino, and R. Noyori, J. Am. Chem., Soc.,100, 1778 (1978).CrossRefGoogle Scholar
  70. 70.
    H. Takaya, J. Hagakawa, S. Makino, and R. Noyori, J. Am. Chem. Soc.,100, 1786 (1978).CrossRefGoogle Scholar
  71. 71.
    R. Noyori, J. Hakagawa, H. Takaya, S. Murai, R. Kobayashi, and N. Sonoda, J. Am. Chem. Soc.,100, 1759 (1978).CrossRefGoogle Scholar
  72. 72.
    R. Funk and K. Vollhardt, J. Am. Chem. Soc.,98, 6755 (1976).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • G. A. Tolstikov
    • 1
  • U. M. Dzhemilev
    • 1
  1. 1.Institute of Chemistry, Bashkir BranchAcademy of Sciences of the USSRUfa

Personalised recommendations