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Chemistry of Natural Compounds

, Volume 18, Issue 2, pp 131–143 | Cite as

Advances in the field of the synthesis of amino derivatives of terpenoids

  • N. G. Kozlov
Article
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Abstract

Information on the synthesis of amino derivatives of monoterpenes by the reduction of oximes by the Leuckart reaction, and by the reductive amination of ketones by amines and nitriles is generalized. The stereochemistry of the amines formed as the result of the above-mentioned reactions is discussed.

Keywords

Oxime Camphor Reductive Amination Menthone Pulegone 

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Literature cited

  1. 1.
    R. Leuckart and E. Bach, Chem. Ber.,20, 104 (1887).CrossRefGoogle Scholar
  2. 2.
    M. O. Forster, J. Chem. Soc., 386 (1889).Google Scholar
  3. 3.
    V. M. Bogoslovskii, in: Reactions and Methods of Investigating Organic Compounds [in Russian], Moscow (1954), p. 255.Google Scholar
  4. 4.
    D. Voisin and B. Gamstambide, Bull. Soc. Chim. Fr.,7, 2643 (1971).Google Scholar
  5. 5.
    K. Alder, G. Stein, and H. Rickert, Ann. Chem.,525, 221 (1936).CrossRefGoogle Scholar
  6. 6.
    A. Daniel and A. Pavia, Bull. Soc. Chim. Fr.,3, 1060 (1971).Google Scholar
  7. 7.
    V. M. Potapov, Stereochemistry [in Russian], Moscow (1976), p. 695.Google Scholar
  8. 8.
    H. Feltkamp, F. Koch, and T. Thanh, Ann. Chem.,707, 95 (1967).CrossRefGoogle Scholar
  9. 9.
    H. Feltkamp, N. Franklin, F. Koch, and T. Thanh, Ann. Chem.,707, 87 (1967).CrossRefGoogle Scholar
  10. 10.
    A. Bose, S. Harrison, and L. Farber, J. Org. Chem.,28, 1223 (1963).CrossRefGoogle Scholar
  11. 11.
    J. King, S. Soo-Khoom, and L. Shiu-Kang, Can. J. Chem.,51, 23, 3914 (1973).CrossRefGoogle Scholar
  12. 12.
    J. Read and R. Storey, J. Chem. Soc., No. 11, 2761 (1930).CrossRefGoogle Scholar
  13. 13.
    J. Read and G. Robertson, J. Chem. Soc., No. 2, 2209 (1926).CrossRefGoogle Scholar
  14. 14.
    H. Feldkamp, F. Koch, and T. Thenh, Ann. Chem.,707, 78 (1967).CrossRefGoogle Scholar
  15. 15.
    J. Read and R. Johnston, J. Chem. Soc., No. 1, 226 (1934).Google Scholar
  16. 16.
    S. Schroeter and E. Eliel, J. Org. Chem.,30, 1 (1965).CrossRefGoogle Scholar
  17. 17.
    R. Johnston and J. Read, J. Chem. Soc., No. 8, 1138 (1935).Google Scholar
  18. 18.
    W. Huckel and W. Doll, Ann. Chem.,526, 103 (1936).CrossRefGoogle Scholar
  19. 19.
    J. Read and G. Swann, J. Chem. Soc., No. 2, 239 (1937).Google Scholar
  20. 20.
    A. Bose, J. Kitsner, and L. Farber, J. Org. Chem.,27, 2925 (1962).CrossRefGoogle Scholar
  21. 21.
    J. Houben, Methoden der Organischen Chemie, Georg Thieme Verlag, Stuttgart (1941).Google Scholar
  22. 22.
    S. Schroeter and E. Eliel, J. Am. Chem. Soc.,86, 2066 (1964).CrossRefGoogle Scholar
  23. 23.
    V. N. Krestinskii and I. I. Bardyshev, Zh. Obshch. Khim.,10, 1894 (1940).Google Scholar
  24. 24.
    J. McKenna and J. Glinger, J. Chem. Soc., No. 8, 2759 (1958).CrossRefGoogle Scholar
  25. 25.
    W. Huckel and G. Meinhardt, Chem. Ber.,90, 2025 (1957).CrossRefGoogle Scholar
  26. 26.
    A. Fry and J. Newberg, J. Am. Chem. Soc.,89, 6374 (1967).CrossRefGoogle Scholar
  27. 27.
    C. Hoffman, US Patent, No. 3,659,015 (1971).Google Scholar
  28. 28.
    Y. Girault, M. Decouzone, and M. Azzaro, Bull. Soc. Chim. Fr., No. 1–2, 385 (1975).Google Scholar
  29. 29.
    F. Winans and H. Adkins, J. Am. Chem. Soc.,55, 2051 (1933).CrossRefGoogle Scholar
  30. 30.
    D. Banthorpe, D. Morris, and C. Bunton, J. Chem. Soc.,C, No. 4, 687 (1971).Google Scholar
  31. 31.
    W. Huckel and J. Sheel, Ann. Chem.,664, 19 (1963).CrossRefGoogle Scholar
  32. 32.
    W. Kokke, J. Org. Chem.,38, 2989 (1973).CrossRefGoogle Scholar
  33. 33.
    D. Cooper and A. Jones, J. Am. Chem. Soc.,23, 3920 (1971).Google Scholar
  34. 34.
    H. Kuczynski, K. Piatkowski, A. Hendrich, and A. Kubik, Tetrahedron Lett., No. 25, 2371 (1967).Google Scholar
  35. 35.
    A. Hendrich and H. Kuchynski, Pol. J. Chem.,41, 2107 (1967).Google Scholar
  36. 36.
    W. Cocker, A. Pratt, and P. Shannone, Tetrahedron Lett., No. 49, 5017 (1967).Google Scholar
  37. 37.
    W. Cocker, A. Pratt, and P. Shannone, J. Chem. Soc.,C, No. 5, 484 (1968).Google Scholar
  38. 38.
    J. Trojanek, J. Pospisek, and Z. Cekan, Collect. Czech. Chem. Commun.,26, 2602 (1961).CrossRefGoogle Scholar
  39. 39.
    W. Mosimann, J. Borgulya, and K. Bernauer, Experientia,25, 726 (1969).CrossRefGoogle Scholar
  40. 40.
    Z. Veydelek and M. Protiva, Collect. Czech. Chem. Commun.,24, 2614 (1959).CrossRefGoogle Scholar
  41. 41.
    A. Ingersoll, J. Brown, C. Kim, et al., J. Am. Chem. Soc.,58, 1808 (1936).CrossRefGoogle Scholar
  42. 42.
    E. Alexander and R. Wildman, J. Am. Chem. Soc.,70, 1187 (1948).CrossRefGoogle Scholar
  43. 43.
    V. Webers and W. Bruce, J. Am. Chem. Soc.,70, 1422 (1948).CrossRefGoogle Scholar
  44. 44.
    W. Davies and W. Rogers, J. Chem. Soc., No. 4, 126 (1944).CrossRefGoogle Scholar
  45. 45.
    C. Pollard and D. Young, J. Org. Chem.,16, 661 (1951).CrossRefGoogle Scholar
  46. 46.
    M. Metaer, Bull. Soc. Chim. France, No. 11–12, 1097 (1948).Google Scholar
  47. 47.
    A. N. Kost, A. P. Terent'ev, and G. A. Shvekhgeimer, USSR Inventor's Certificate No. 85,828, Byull. Isobret., No. 12 (1950).Google Scholar
  48. 48.
    J. Read and A. Cook, J. Chem. Soc., 2223 (1926).CrossRefGoogle Scholar
  49. 49.
    J. Blanc, P. Carnero, and B. Gastambide, Bull. Soc. Chim. Fr.,8, 1864 (1964).Google Scholar
  50. 50.
    W. Huckel and P. Rieckman, Ann. Chem.,625, 1 (1959).CrossRefGoogle Scholar
  51. 51.
    A. Ingersoll and H. DeWitt, J. Am. Chem. Soc.,73, 3360 (1951).CrossRefGoogle Scholar
  52. 52.
    K. Rubinstein, N. Elming, and J. Fakstop, Acta Chem. Scand.,17, 2079 (1963).CrossRefGoogle Scholar
  53. 53.
    H. Dickison and A. Ingersoll, J. Am. Chem. Soc.,61, 2477 (1939).CrossRefGoogle Scholar
  54. 54.
    E. Massey, H. Smith, and A. Gordon, J. Org. Chem. Soc.,31, 684 (1966).CrossRefGoogle Scholar
  55. 55.
    H. Smith, J. Brand, E. Massey, and I. Durham, J. Org. Chem.,31, 690 (1966).CrossRefGoogle Scholar
  56. 56.
    J. Bunnet and J. Marks, J. Am. Chem. Soc.,71, 1587 (1949).CrossRefGoogle Scholar
  57. 57.
    L. Goodson, C. Wiegand, and J. Aplitter, J. Am. Chem. Soc.,68, 2174 (1946).CrossRefGoogle Scholar
  58. 58.
    P. Smith and A. MacDonald, J. Am. Chem. Soc.,72, 1037 (1950).CrossRefGoogle Scholar
  59. 59.
    O. Walach, Ann. Chem.,343, 55 (1905).Google Scholar
  60. 60.
    G. Stein, M. Sletziner, H. Arnold et al., J. Am. Chem. Soc.,78, 1514 (1956).CrossRefGoogle Scholar
  61. 61.
    T. Takahashi, M. Hori, Y. Suzuki, and Y. Hamashima, J. Pharm. Soc. Jpn.,79, 162 (1959).CrossRefGoogle Scholar
  62. 62.
    L. Luskin, A. McFaul, and G. Gantert, J. Org. Chem.,21, 1430 (1956).CrossRefGoogle Scholar
  63. 63.
    A. Pancrazi, J. Kobore, and Q. Khong-Huu, Bull. Soc. Chim. Fr., No. 2, 162 (1977).Google Scholar
  64. 64.
    J. Kae and J. Linsk, J. Chem. Soc., 6978 (1963).Google Scholar
  65. 65.
    A. Le Bris, G. Lefebre, and F. coussemant, Bull. Soc. Chim. Fr., No. 7, 1584 (1964).Google Scholar
  66. 66.
    S. Kiyoka and S. Suzuki, Bull. Soc. Chem. Jpn.,47, 2081 (1974).CrossRefGoogle Scholar
  67. 67.
    N. Mueller and J. Paust, GFR Patent No. 2,545,657 (1977).Google Scholar
  68. 68.
    T. Kralt, H. Moed, and J. Dijk, Rec. Trav. Chim.,77, 177 (1958).CrossRefGoogle Scholar
  69. 69.
    H. Moed, T. Kralt, and J. Dijk, Rec. Trav. Chim.,77, 196 (1958).CrossRefGoogle Scholar
  70. 70.
    T. Kralt, Rec. Trav. Chim.,77, 990 (1958).CrossRefGoogle Scholar
  71. 71.
    H. Weingarten, J. Chupp, and W. White, J. Org. Chem.,32, 3246 (1967).CrossRefGoogle Scholar
  72. 72.
    W. Taub and M. Avramoff, US Patent No. 3,770,825 (1973).Google Scholar
  73. 73.
    T. Takeshite and M. Kitajima, J. Chem. Soc. Jpn.,81, 1284 (1960).Google Scholar
  74. 74.
    A. Donetti, S. Casadio, C. Molino, et al., J. Med. Chem.,15, 1088 (1972).CrossRefGoogle Scholar
  75. 75.
    J. Soloducho and A. Zabza, Pol. J. Chem.,53, 1497 (1979).Google Scholar
  76. 76.
    N. V. Kuznetsov, N. V. Mikryukova, and R. Yu. Selens, Republic Intercollegiate Conference on Physiological Active Substances [in Russian], Moscow, No. 9 (1977), p. 27.Google Scholar
  77. 77.
    M. Kreevoy and R. Borch, US Patent No. 3,873,621 (1975).Google Scholar
  78. 78.
    A. A. Svishchuk, N. K. Makhnovskii, and N. Kh. Mikryukova, Usp. Khim. Zh.,43, 173 (1977).Google Scholar
  79. 79.
    S. Markowich and B. Bochvic, Pol. J. Chem.,52, 671 (1978).Google Scholar
  80. 80.
    S. I. Kozintsev, Author's Abstract of Candidate's Dissertation, Minsk (1975).Google Scholar
  81. 81.
    N. S. Kozlov and S. I. Kozintsev, USSR Inventor's Certificate No. 455,944, Byull. Izobret., No. 1 (1975).Google Scholar
  82. 82.
    N. S. Kozlov, S. I. Kozintsev, and L. V. Naumova, Dokl. Akad. Nauk SSSR,226, 1341 (1976).Google Scholar
  83. 83.
    N. S. Kozlov, L. I. Moiseenok, and S. I. Kozintsev, Dokl. Akad. Nauk. SSSR,241, 1345 (1978).Google Scholar
  84. 84.
    N. S. Kozlov, L. I. Moiseenok, and S. I. Kozintsev, USSR Inventor's Certificate No. 620,477, Byull Izobret., No. 31 (1978).Google Scholar
  85. 85.
    N. S. Kozlov and S. I. Kozintsev, USSR Inventor's Certificate No. 517,580, Byull. Izobret., No. 22 (1976).Google Scholar
  86. 86.
    I. I. Bardyshev, N. G. Kozlov, T. I. Pekhk, and T. K. Vyalimyaé, Izv. Akad. Nauk BSSR, Ser. Khim., No. 4, 71 (1980).Google Scholar
  87. 87.
    I. I. Bardyshev, N. G. Kozlov, and A. A. Geller, USSR Inventor's Certificate No. 825,504 (1981).Google Scholar
  88. 88.
    E. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York (1962).Google Scholar
  89. 89.
    I. I. Bardyshev, N. G. Kozlov, T. K. Vyalimyaé, and T. I. Pekhk, Khim. Prir. Soedin., 546 (1980).Google Scholar
  90. 90.
    I. I. Bardyshev and N. G. Kozlov, USSR Inventor's Certificate No. 765,257, Byull. Izobr., No. 35 (1980).Google Scholar
  91. 91.
    H. Becker, Einführung in die Elektroentheorie Organisch-chemischer Reaktionen, 3rd. edn., VEB Deutscher Verlag der Wissenshaften, Berlin (1974).Google Scholar
  92. 92.
    I. I. Bardyshev, N. G. Kozlov, and A. A. Geller, Izv. Akad. Nauk BSSR, Ser. Khim., No. 3, 116 (1979).Google Scholar
  93. 93.
    N. S. Kozlov, V. A. Tarasevich, and S. I. Kozintsev, Dokl. Akad. Nauk SSSR,244, 1130 (1979).Google Scholar
  94. 94.
    N. S. Kozlov, V. A. Tarasevich, S. I. Kozintsev, and L. V. Gladkikh, Dokl. Akad. Nauk BSSR,23, 910 (1979).Google Scholar
  95. 95.
    I. I. Bardyshev and N. G. Kozlov, Dokl. Akad. Nauk BSSR,23, 630 (1979).Google Scholar
  96. 96.
    M. Freifelder, Practical Catalytic Hydrogenation, Wiley, New York (1970), p. 333.Google Scholar
  97. 97.
    H. Kreiger, “Arzneimittelforschung an Norboran-Derivaten,” Arzneim-Forsch. (Drug. Res.), 129 (1968).Google Scholar
  98. 98.
    H. Hisae, Y. Hideo, Y. Takashi, and T. Saburo, Agr. Biol. Chem.,38, 141 (1974).CrossRefGoogle Scholar

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© Plenum Publishing Corporation 1983

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  • N. G. Kozlov

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