Skip to main content
Log in

One-pot amination of cage hydrocarbons

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A one-pot procedure has been proposed for the synthesis of amines directly from cage hydrocarbons. A number of cage amines have been synthesized by treatment of adamantane, its homologs, and structurally related cage hydrocarbons with nitric acid in acetic acid and subsequent addition of urea and heating.

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. Liu, J., Obando, D., Liao, V., Lifa, T., and Codd, R., Eur. J. Med. Chem., 2011, vol. 46. p. 1949.

    Article  CAS  Google Scholar 

  2. Cates, L.A., Gallio, R.L., and Cramer, M.B., J. Pharm. Sci., 1973, vol. 62. p. 1719.

    Article  CAS  Google Scholar 

  3. Rojas, P., Altagracia, M., Kravzov, J., and Rios, C., Drug Dev. Res., 1993, vol. 29. p. 222.

    Article  CAS  Google Scholar 

  4. Maj, J., Arzneim. Forsch., 1982, vol. 32. p. 1256.

    CAS  Google Scholar 

  5. Brown, F. and Redfern, P.H., Br. J. Pharmacol., 1976, vol. 58. p. 561.

    Article  CAS  Google Scholar 

  6. Stoof, J.C., Booij, J., Drukarch, B., and Wolters, E.C., Eur. J. Pharmacol., 1992, vol. 213, p. 439.

    Article  CAS  Google Scholar 

  7. Wesemann, W., Sontag, K.H., and Maj, J., Arzneim. Forsch., 1983, vol. 33. p. 1122.

    CAS  Google Scholar 

  8. Fleischhacker, W.W., Buchgeher, A., and Schubert, H., Prog. Neuro-Psychopharmacol. Biol. Psychiatry, 1986, vol. 10. p. 87.

    Article  CAS  Google Scholar 

  9. Joubert, J., Geldenhuys, W.J., Van der Schyf, C.J., Oliver, D.W., Kruger, H.G., Govender, T., and Malan, S.F., Chem.Med.Chem., 2012, vol. 7. no. 3. p. 375.

    Article  CAS  Google Scholar 

  10. Spasov, A.A., Khamidova, T.V., Bugaeva, L.I., and Morozov, I.S., Pharm. Chem. J., 2000, vol. 34. no. 1. p. 1.

    Article  CAS  Google Scholar 

  11. Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev., 2013, vol. 113, p. 3516.

    Article  CAS  Google Scholar 

  12. Duque, M.D., Torres, E., Valverde, E., Barniol, M., Guardiola, S., Rey, M., and Vázquez, S., Recent Advances in Pharmaceutical Sciences, Muñoz-Torrero, D., Ed., Trivandrum, Kerala, India: Transworld Research Network, 2011, p. 35.

  13. Klimochkin, Yu.N., Shiryaev, V.A., and Leonova, M.V., Izv. Akad. Nauk, Ser. Khim., 2015, p. 1473.

    Google Scholar 

  14. De Clercq, E., Nat. Rev. Drug Discovery, 2006, vol. 5. p. 1015.

    Article  Google Scholar 

  15. Kolocouris, N., Zoidis, G., Foscolos, G.B., Fytas, G., Prathalingham, S.R., Kelly, J.M., Naesens, L., and De Clercq, E., Bioorg. Med. Chem. Lett., 2007, vol. 17. p. 4358.

    Article  CAS  Google Scholar 

  16. Zoidis, G., Tsotinis, A., Kolocouris, N., Kelly, J.M., Prathalingam, S.R., Naesens, L., and De Clercq, E., Org. Biomol. Chem., 2008, vol. 6. p. 3177.

    Article  CAS  Google Scholar 

  17. Kelly, J.M., Miles, M.A., and Skinner, A.C., Antimicrob. Agents Chemother., 1999, vol. 43. p. 985.

    CAS  Google Scholar 

  18. Kelly, J.M., Quack, G., and Miles, M.M., Antimicrob. Agents Chemother., 2001, vol. 45. p. 1360.

    Article  CAS  Google Scholar 

  19. Fort, R.C., Jr., Adamantane. The Chemistry of Diamond Molecules, New York: Marcel Dekker, 1976.

    Google Scholar 

  20. Bagrii, E.I., Adamantany (Adamantanes), Moscow: Nauka, 1989.

    Google Scholar 

  21. Olah, G.A., Cage Hydrocarbons, New York: Wiley, 1990.

    Google Scholar 

  22. Carbocyclic Cage Compounds: Chemistry and Applications, Osawa, E.J. and Yonemitsu, O., New York: VCH, 1992.

  23. Kovacic, P. and Roskos, P.D., Tetrahedron Lett., 1968, vol. 56. p. 5833.

    Article  Google Scholar 

  24. Kovacic, P. and Roskos, P.D., J. Am. Chem. Soc., 1969, vol. 91. p. 6457.

    Article  CAS  Google Scholar 

  25. Norcliffe, J.L., Conway, L.P., and Hodgson, D.R.W., Tetrahedron Lett., 2011, vol. 52. p. 2730.

    Article  CAS  Google Scholar 

  26. Park, K.K., Oh, C.H., and Sim, W.-J., J. Org. Chem., 1995, vol. 60. p. 6202.

    Article  CAS  Google Scholar 

  27. Shimizu, Y., Morimoto, H., Zhang, M., and Ohshima, T., Angew. Chem., Int. Ed., 2012, vol. 51. p. 8564.

    Article  CAS  Google Scholar 

  28. Jirgensons, A., Kauss, V., Kalvinsh, I., and Gold, M.R., Synthesis, 2000, p. 1709.

    Google Scholar 

  29. Butov, G.M., Pershin, V.V., and Burmistrov, V.V., RU Patent no. 244. 971, 2012; Byull. Izobret., 2012, no. 3.

    Google Scholar 

  30. Ivleva, E.A., Ovchinnikov, K.A., and Klimochkin, Yu.N., RU Patent no. 254. 545, 2015; Byull. Izobret., 2015, no. 5.

    Google Scholar 

  31. Moiseev, I.K., Bagrii, E.I., Klimochkin, Yu.N., Dolgopolova, T.N., Trakhtenberg, P.L., and Zemtsova, M.N., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985, vol. 34. no. 9. p. 1980.

    Article  Google Scholar 

  32. Moiseev, I.K., Klimochkin, Yu.N., Zemtsova, M.N., and Trakhtenberg, P.L., Zh. Org. Khim., 1984, vol. 20. p. 1435.

    CAS  Google Scholar 

  33. Klimochkin, Yu.N. and Moiseev, I.K., Zh. Org. Khim., 1987, vol. 23. p. 2025.

    CAS  Google Scholar 

  34. Moiseev, I.K., Klimochkin, Yu.N., Bagrii, E.I., and Dolgopolova, T.N., USSR Inventor’s Certificate no. 124. 900, 1986; Byull. Izobret., 2006, no. 23.

    Google Scholar 

  35. Klimochkin, Yu.N., Bagrii, E.I., Dolgopolova, T.N., and Moiseev, I.K., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, vol. 37. no. 4. p. 757.

    Article  Google Scholar 

  36. Klimochkin, Yu.N., Moiseev, I.K., Vladyko, G.V., Korobchenko, L.V., and Boreko, E.I., Pharm. Chem. J., 1991, vol. 25. no. 7. p. 485.

    Article  Google Scholar 

  37. Klimochkin, Yu.N., Moiseev, I.K., Boreko, E.I., Vladyko, G.V., and Korobchenko, L.V., Pharm. Chem. J., 1989, vol. 23. no. 4. p. 418.

    Article  CAS  Google Scholar 

  38. Burhchard, J. and Landa, S., Sb. Vys. Sk. Chem.-Technol. Praze, C: Org. Chem. Technol., 1973, vol. 29. p. 91.

    Google Scholar 

  39. Korolev, B.A., Khardin, A.P., Radchenko, S.S., Novakov, I.A., and Orlinson, B.S., Zh. Org. Khim., 1978, vol. 14. p. 1632.

    CAS  Google Scholar 

  40. Moiseev, I.K., Klimochkin, Yu.N., and Kumerov, G.F., USSR Inventor’s Certificate no. 1338334, 1987; Byull. Izobret., 2006, no. 36.

    Google Scholar 

  41. Klimochkin, Yu.N., Leonova, M.V., and Timofeeva, A.K., RU Patent no. 2246482, 2005; Byull. Izobret., 2005, no. 5.

    Google Scholar 

  42. Bormann, J., Gold, M.R., and Schatton, W., US Patent no. 506. 703, 1991; Chem. Abstr., 1991, vol. 115, no. 22. 31 b.

    Google Scholar 

  43. Krishnamurthy, V.V., Iyer, P.S., and Olah, G.A., J. Org. Chem., 1983, vol. 48. p. 3373.

    Article  CAS  Google Scholar 

  44. Ashraf, N. and Abdel-Sayed, B.L., Tetrahedron Lett., 1986, vol. 27. p. 1003.

    Article  Google Scholar 

  45. Cahill, P.A., Tetrahedron Lett., 1990, vol. 31. p. 5417.

    Article  CAS  Google Scholar 

  46. Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 2. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1983, vol. 4. p. 568.

  47. Horn, E.-M., Keiser, H., and Schoeller, K., Monatsh. Chem., 1987, vol. 118, p. 1205.

    Article  CAS  Google Scholar 

  48. Stetter, H., Mayer, J., Schwarz, M., and Wulff, K., Chem. Ber., 1960, vol. 93. p. 226.

    Article  CAS  Google Scholar 

  49. Henkel, J.C., Hane, J.T., and Gianutsos, G., J. Med. Chem., 1982, vol. 25. p. 51.

    Article  CAS  Google Scholar 

  50. Chervinka, O., Kriz, O., Hala, S., and Landa, S., Z. Chem., 1971, vol. 11. p. 382.

    Article  Google Scholar 

  51. Sasaki, T., Equchi, S., Toru, T., and Ito, K., Bull. Chem. Soc. Jpn., 1970, vol. 43. p. 1820.

    Article  CAS  Google Scholar 

  52. Sasaki, T., Equchi, S., Katada, T., and Hiroaki, O., J. Org. Chem., 1977, vol. 42. p. 3741.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. V. Leonova.

Additional information

Original Russian Text © M.V. Leonova, M.Yu. Skomorokhov, I.K. Moiseev, Yu.N. Klimochkin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 12, pp. 1737–1743.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Leonova, M.V., Skomorokhov, M.Y., Moiseev, I.K. et al. One-pot amination of cage hydrocarbons. Russ J Org Chem 51, 1703–1709 (2015). https://doi.org/10.1134/S1070428015120064

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428015120064

Keywords

Navigation