Skip to main content
Log in

An up-to-date analysis of the chemistry of piperideine-3 (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The chemistry of piperideine-3 and its derivatives is generally linked with the synthesis of biologically active substances and medicinale. This review discusses the most interesting chemical reactions of piperideine-3 and its derivatives which have been discovered in the last 10–15 years.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Yu. A. Berlin and A. N. Kost, Usp. Khim., 29, 220 (1966).

    Google Scholar 

  2. M. Ferles and J. Plimt, Adv. Heterocycl. Chem, 128, 43 (1970).

    Google Scholar 

  3. R. T. Courts and J. R. Scott, Can. J. Pharm. Sci., 6, 78 (1971).

    Google Scholar 

  4. A. P. Orekhova. Chemistry of Alkaloids [in Russian], USSR Academy of Sciences Press, Moscow, 1955.

    Google Scholar 

  5. B. Burns, C. Chiueh, S. Markey, M. Ebert, D. Jacobowitz, and T. Kopin, Proc. Natl. Acad. Sci. USA, 80, 4546 (1983).

    Google Scholar 

  6. J. Langston, P. Ballard, J. Tetrud, and I. Irwin, Science, 219, 979 (1983).

    Google Scholar 

  7. R. Heikkila, A. Hess, and T. Duvoisin, Life Sci., 36, 231 (1985).

    Google Scholar 

  8. S. O. Bachurin, S. O. Sablin, G. V. Grishina, E. L. Gaidarova, L. G. Dubova, and N. D. Zubov, Bioorg. Khim., 15, 620 (1989).

    Google Scholar 

  9. J. Javitch, R. D'Amato, S. Strittmater, and S. Snydar, Proc. Nat. Acad. Sci. USA, 82, 2173 (1985).

    Google Scholar 

  10. S. O. Bachurin, L. S. Solyakov, N. N. Lermontova, S. E. Tkachenko, V. V. Kalashnikov, T. P. Serkova, and L. P. Petrova, Dokl. Akad. Nauk SSSR., 307, No. 3, 740 (1989).

    Google Scholar 

  11. T. Nagatsu and T. Hirata, Eur. Neurol., 26, Suppl. 1, 11 (1987).

    Google Scholar 

  12. W. Nicklas, J. Vyas, and R. Heikkila, Life Sci., 36, 2503 (1985).

    Google Scholar 

  13. H. Kinemuchi, C. Fowler, and K. Tipton, Neurochem. Int., 11, 359 (1987).

    Google Scholar 

  14. T. Nagatsu, Asian Med. J., 6, 304 (1989).

    Google Scholar 

  15. A. Barbeau, M. Roy, T. Cloutier, L. Plasse, and S. Paris, Advances in Neurology, Vol. 45, Raven Press, New York (1986), p. 249.

    Google Scholar 

  16. C. Tanner, TINS, 12, 4954 (1989).

    Google Scholar 

  17. S. O. Bachurin, S. E. Tkachenko, and N. N. Lermontova, Rev. Environ. Contam. Toxicol., 122, 33 (1991).

    Google Scholar 

  18. W. Gessne, Helv. Chim. Acta, 67, 2057 (1984).

    Google Scholar 

  19. A. Aibb, Neurosci. Lett., 76, 316 (1987).

    Google Scholar 

  20. D. M. Zimmerman, B. E. Cantrell, J. K. Reel, S. K. Hemrickluecke, and R. W. Fuller, J. Med. Chem., 29, 1517 (1986).

    Google Scholar 

  21. P. K. Sonsalla, J.Pharmacol. Exp. Ther., 242, No. 3, 850 (1987).

    Google Scholar 

  22. A. Brossi, J. Med. Chem., 29, 444 (1986)

    Google Scholar 

  23. A. Ziering, L. Berger, S. Heinman, and J. Lee, J. Org. Chem., 12, 894 (1947).

    Google Scholar 

  24. S. McElvain and J. Safranski, J. Am. Chem. Soc., 72, 3134 (1950).

    Google Scholar 

  25. A. F. Casey, A. H. Beckett, M. A. Fovig, and H. J. Yousset, Tetrahedron, 12, 3387 (1965).

    Google Scholar 

  26. D. A. Evans and C. H. Mitch, Tetrahedron Lett., 23, 285 (1982).

    Google Scholar 

  27. C. J. Barnett, C. R. Copely-Merriman, and J. Makig, J. Org. Chem., 54, 4075 (1989).

    Google Scholar 

  28. J. C. Jaen and L. D. Wise, J. Heterocycl. Chem., 24, 1317 (1987).

    Google Scholar 

  29. N. S. Prostakov and L. A. Gaivoronskaya, Usp. Khim., 47, 859 (1978).

    Google Scholar 

  30. R. Lyle and P. Anderson, Adv. Heterocycl. Chem., 6, 45 (1966).

    Google Scholar 

  31. P. S. Anderson, W. E. Kueger, and E. L. May, Tetrahedron Lett., 6, 4011 (1965)

    Google Scholar 

  32. K. C. Rice, A. E. Jacobson and E. L. May, J. Med. Chem., 18, 854 (1975).

    Google Scholar 

  33. E. Reimann, I. Schwaltzer, and F. Zymalkowski, Lieb. Ann. Chem., No. 5/6, 1070 (1975).

    Google Scholar 

  34. E. Reimann, Lieb. Ann. Chem., No. 12, 1963 (1978).

    Google Scholar 

  35. J. Bosch, O. Mauleon, F. Boncompte, and S. Granados, J. Heterocycl. Chem., 18, 263 (1981).

    Google Scholar 

  36. E. Reimann and A. Baney, Arch. Pharm., 317, 517 (1984).

    Google Scholar 

  37. E. Reimann, J. Speckbacher, and H. Letter, Arch. Pharm., 320, 385 (1987).

    Google Scholar 

  38. W. Gessner and A. Brossi, Synth. Commun., 15, 911 (1985).

    Google Scholar 

  39. R. O. Hutchins and N. R. Natale, Synthesis, No. 4, 281 (1979).

    Google Scholar 

  40. S. M. McElvain and R. S. Berger, J. Am. Chem. Soc., 77, 2848 (1955).

    Google Scholar 

  41. D. Berney, Helv. Chim. Acta, 61, 1110 (1978).

    Google Scholar 

  42. F. Hauhe and F. Zymaikowski, Arch. Pharm., 312, 477 (1970).

    Google Scholar 

  43. C. J. Schmidle and R. C. Mansfield, J. Am. Chem. Soc., 77, 5698 (1955).

    Google Scholar 

  44. C. J. Schmidle and R. C. Mansfield, J. Am. Chem. Soc., 78, 425 (1956).

    Google Scholar 

  45. C. J. Schmidle and R. C. Mansfield, J. Am. Chem. Soc., 78, 1702 (1956).

    Google Scholar 

  46. R. Merten and A. Miller, Angew. Chem., 74, 866 (1962).

    Google Scholar 

  47. H. Bohme, K. Hartke, and A. Muller, Chem. Ber., 96, 607 (1963).

    Google Scholar 

  48. T. N. Maksimova, I. B. Mokhalin, and B. V. Unkovskii. Tr. Mosk. Inst. Tonk. Khim. Tekh., 5, 38 (1975).

    Google Scholar 

  49. Ger. Pat. 106,374 (H. Zinner, W. E. Siems, and D. Luedtke), Chem. Abs., 81, 152007t (1974).

    Google Scholar 

  50. Ger. Offen. 2,372,643 (S. Tanaka, M. Kakimoto, and J. Ikeda), Chem. Abs., 88, 105179k (1978).

    Google Scholar 

  51. O. L. Scott and A. G. Paul, J. Am. Chem. Soc., 107, 1768 (1985).

    Google Scholar 

  52. S. F. McCann and L. E. Overmann, J. Am. Chem. Soc., 109, 6107 (1987).

    Google Scholar 

  53. C. J. Flann and L. E. Overmann, J. Am. Chem. Soc., 109, 6115 (1987)

    Google Scholar 

  54. S. Mogeswavan, W. O. Ollis, and I. O. Sutherland, J. Chem. Soc., Perkin I., No. 7, 1953 (1981).

    Google Scholar 

  55. H. Sashida and T. Tsuchiya, Heterocycles, 19, 28 (1982).

    Google Scholar 

  56. H. Sashida and T. Tsuchiya, Chem. Pharm. Bull., 32, 4117 (1984).

    Google Scholar 

  57. J. Bosch, J. Canals, and R. Granados, J. Heterocycl. Chem., 12, 1117 (1975).

    Google Scholar 

  58. J. Bosch, J. Canals, and R. Granados, Quim. Anal., 71, 253 (1975).

    Google Scholar 

  59. D. C. Palmer and M. J. Strauss, Chem. Rev., 7(1), 1 (1977).

    Google Scholar 

  60. N. Yokogama and P. I. Almanla, J. Med. Chem., 22, 537 (1979).

    Google Scholar 

  61. Ger. Offen. 2,348.95 (F. P. Hauck and J. E. Sundeen), Chem. Abs., 81, 3777s (1974).

  62. US Pat. 3,953,434 (F. P. Hauck and J. E. Sundeen), Chem. Abs., 85, 108555d (1976).

    Google Scholar 

  63. US Pat. 3,965,102 (F. P. Hauck and J. E. Sundeen), Chem. Abs., 85, 159914c (1976).

    Google Scholar 

  64. E. Bellova, B. Cereda, and A. Donetti, Org. Prep. Proced. Int., 8, 443 (1976).

    Google Scholar 

  65. Ger. Offen. 2,415,124 (K. Kobayashi, T. Fukumaru, H. Muzote, S. Inaba and H.Yamamoto), Chem. Abs., 82 (1975).

  66. Jap. Kokai 82.074 (Y. Kato, K. Yoshikawa, I. Nakajime, and T. Shinichi), Chem. Abs., 84, 5228z (1976).

    Google Scholar 

  67. N. F. Albertson, W. F. Michne, and B. E. Tullar, J. Med. Chem., 21, 471 (1978).

    Google Scholar 

  68. P. Jimonet, D. S. Crierson, and H. P. Husson, Tetrahedron Lett., 28, 6179 (1987).

    Google Scholar 

  69. N. Yokogama, F. B. Block, and F. H. Clarke, J. Med. Sci., 13, 488 (1970).

    Google Scholar 

  70. T. Kametani and T. Honda, Can. J. Chem., 53, 3820 (1975).

    Google Scholar 

  71. M. Alvaros, J. Bosch, R. Granados, and F. Lopes, J. Heterocycl. Chem., 15, 193 (1978).

    Google Scholar 

  72. J. Bosch, P. Manleon, F. Boncompte, and R. Granados, J. Heterocycl. Chem., 18, 263 (1981).

    Google Scholar 

  73. J. Benjoch, F. Boncompte, and N. Casumitju, Tetrahedron, 42, 6693 (1986).

    Google Scholar 

  74. M. G. Bevetta, B. Rindone, C. Scdastico, and C. Tronconi, Synthesis, No. 7, 440 (1975).

    Google Scholar 

  75. Jap. Pat. 75 49.297 (M. Kimora, T. Nakajima, S. Inaba, and H. Iamamat, Chem. Abs., 83, 193092b (1975).

    Google Scholar 

  76. M. Kimura, T. Nakajima, S. Inaba, and H. Yamamoto, Chem. Pharm. Bull., 24, 515 (1976).

    Google Scholar 

  77. M. Kimura, Chem. Pharm. Bull., 23, 3208 (1975).

    Google Scholar 

  78. H. Schaefer, Arzneim.-Forsch., 34, 233 (1984).

    Google Scholar 

  79. S. J. Martinez and J. A. Joule, Tetrahedron, 34, 3027 (1978).

    Google Scholar 

  80. P. Becken and F. W. Fowler, J. Org. Chem., 45, 1336 (1980).

    Google Scholar 

  81. K. T. Wonner and A. Kaerner, Heterocycles, 26, 917 (1987).

    Google Scholar 

  82. US Pat. 3,824,242 (R. Levin and V. Bell), Chem. Abs., 81 (1974).

  83. D. A. Evans, C. H. Mitch, R. C. Thomas, D. M. Zimmerman, and R. L. Robey, J. Am. Chem. Soc., 102, 5955 (1980).

    Google Scholar 

  84. D. A. Evans and C. H. Mitch, Tetrahedron Lett., 23, 285 (1982).

    Google Scholar 

  85. A. B. Shehvi and E. Giganek, J. Org. Chem., 49, 2942 (1984).

    Google Scholar 

  86. D. K. Zimmerman, B. E. Cantrell, J. K. Reel, S. K. Hemrick-Luecke, and R. W. Fuller, J. Med. Chem., 29, 1517 (1986).

    Google Scholar 

  87. D. K. Zimmerman, B. E. Cantrell, J. K. Schwartzendruber, N. D. Jones, L. G. Mendelsohn, J. D. Leander, and R. C. Nickander, J. Med. Chem., 31, 555 (1988).

    Google Scholar 

  88. B. E. Cantrell, J. W. Paschal, and D. M. Zimmerman, J. Org. Chem., 54, 1442 (1989).

    Google Scholar 

  89. C. J. Barnett, C. R. Copley-Merriman, and J. Maki, J. Org. Chem., 54, 4795 (1989).

    Google Scholar 

  90. US Pat 4,081,450 (D. M. Zimmerman), Chem. Abs., 89 (1978).

  91. E. E. Suggand P. S. Portoghese, J. Med. Chem., 29, 2028 (1986).

    Google Scholar 

  92. D. S. Grierson, M. Harris, and H.-P. Husson, J. Am. Chem. Soc. 102, 1064 (1980).

    Google Scholar 

  93. M. Bonin, J. R. Romero, D. S. Grierson, and H.-P. Husson, Tetrahedron Lett., 23, 3369 (1982).

    Google Scholar 

  94. M. Bonin, R. Besselievre, D. S. Grierson, and H.-P. Husson, Tetrahedron Lett., 24, 1493 (1983).

    Google Scholar 

  95. M. Harries, D. S. Grierson, and H.-P. Husson, Tetrahedron Lett., 22, 1511 (1981).

    Google Scholar 

  96. M. Bonin, J. Royer, D. S. Grierson, and H.-P. Husson, Tetrahedron Lett., 27, 1569 (1986).

    Google Scholar 

  97. M. Mehmandoust, C. Mavazano, and B. C. Das, J. Chem. Soc., Chem. Commun., No. 16, 1185 (1989).

    Google Scholar 

  98. A. I. Meyers, P. D. Edwards, W. F. Ricker, and T. R. Bailey, J. Am. Chem. Soc., 106, 3270 (1984).

    Google Scholar 

  99. A. I. Meyers, D. A. Pickman and T. R. Bailey, J. Am. Chem. Soc., 107, 7974 (1985).

    Google Scholar 

  100. M. F. Loewe, M. Boes, and A. I. Meyers, Tetrahedron Lett., 26, 3295 (1985).

    Google Scholar 

  101. A. I. Meyers and L. M. Fuentes, J. Am. Chem. Soc., 105, 118 (1983).

    Google Scholar 

  102. A. I. Meyers, L. M. Fuentes, and Y. Kubota, Tetrahedron, 40, 1361 (1984).

    Google Scholar 

  103. A. I. Meyers and J. Gulles, Heterocycles, 28, 295 (1989).

    Google Scholar 

  104. M. F. Loewe and A. I. Meyers, Tetrahedron Lett., 26, 3291 (1985).

    Google Scholar 

  105. A. I. Meyers and D. B. Miller, J. Am. Chem. Soc., 110, 4778 (1988).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Dedicated to Professor A. R. Katritsky on his 65th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 913–936, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Grishina, G.V., Bachurin, S.O., Tkachenko, S.E. et al. An up-to-date analysis of the chemistry of piperideine-3 (review). Chem Heterocycl Compd 29, 775–795 (1993). https://doi.org/10.1007/BF00528889

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00528889

Keywords

Navigation