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Russian Journal of Organic Chemistry

, Volume 54, Issue 8, pp 1127–1133 | Cite as

Synthesis of N-(Adamantan-1-yl)carbamides by Ritter Reaction from Adamantan-1-ol and Nitriles in the Presence of Cu-Catalysts

  • A. R. Bayguzina
  • A. R. Lutfullina
  • R. I. Khusnutdinov
Article
  • 29 Downloads

Abstract

A selective synthesis of (Z)-N-(adamantan-1-yl)carbamides by the reaction of adamantan-1-ol and nitriles in the presence of Cu catalysts was carried out. Z-Conformation of amides is established basing on X-ray diffraction analysis and 2D NMR data.

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References

  1. 1.
    Bagrii, E.I., Adamantany (Adamantanes), Moscow: Nauka, 1989.Google Scholar
  2. 2.
    Krumkalns, E., Brindle, R., Marshall, F., and Root M., J. Med. Chem., 1963, vol. 6, p.760.CrossRefPubMedGoogle Scholar
  3. 3.
    Kovtun, V.Yu. and Plakhotnik, V.M., Pharm. Chem. J., 1987, vol. 21, p. 555. doi 10.1007/BF00759430CrossRefGoogle Scholar
  4. 4.
    Isaev, S.D., Yurchenko, A.G., and Isaeva, S.S., Fiziol. Aktivn. Veshch., 1983, vol. 15, p.3.Google Scholar
  5. 5.
    Gerson, K., Tobias, D.J., Holmes, R.I., Rathbun, R.I., and Kattau, R.W., J. Med. Chem., 1967, vol. 10, p. 603. doi 10.1021/jm00316a018CrossRefGoogle Scholar
  6. 6.
    Shokova, E., Mousoulou, T., Luzikov, V., and Kovalev, V., Synthesis, 1997, p. 1034.Google Scholar
  7. 7.
    Olah, G.A. and Balaram Gupta, B.G., J. Org. Chem., 1980, vol. 45, p. 3532.CrossRefGoogle Scholar
  8. 8.
    Engel, P.S., Lee, W.-K., Marschke, G.E., and Shine, H.J., J. Org. Chem., 1987, vol. 52, p. 2813.CrossRefGoogle Scholar
  9. 9.
    Haaf, W., Chem. Ber., 1963, vol. 96, p. 3359.CrossRefGoogle Scholar
  10. 10.
    Sztaricskai, F., Pelyvas, J., Dinya, Z., Szilagyi, L., Gyorgydeak, Z., Hadhazy, Gy., and Vaczi, L., Pharmazie, 1975, vol. 30, p.57.Google Scholar
  11. 11.
    Olah, G.A., Balaram Gupta, B.G., and Narang, S.C., Synthesis, 1979, p.274.Google Scholar
  12. 12.
    Plakhotnik, V.M., Kovtun, V.Yu., and Yashunskii, V.G., Zh. Org. Khim., 1982, vol. 18, p. 1001.Google Scholar
  13. 13.
    D'Angelo, J.G., Cody, J.A., Larrabee, C., Ostrander, D.J., Rugg, K.W., and Donna Mamangun, D., Synth. Commun., 2013, vol. 43, p. 3224.CrossRefGoogle Scholar
  14. 14.
    Dokli, I. and Gredicak, M., Eur. J. Org. Chem., 2015, vol. 12, p. 2727.CrossRefGoogle Scholar
  15. 15.
    Lakouraj, M.M. and Mokhtary, M., Monatsh. Chem., 2009, vol. 140, p.53.CrossRefGoogle Scholar
  16. 16.
    Polshettiwar, V. and Varma, R.S., Tetrahedron Lett., 2008, vol. 49, p. 2661.CrossRefGoogle Scholar
  17. 17.
    Martinez, A.G., Alvarez, R.M., Vilar, E.T., Fraile, A.G., Hanack, M., and Subramanian, L.R., Tetrahedron Lett., 1989, vol. 30, p.581.CrossRefGoogle Scholar
  18. 18.
    Yaragorla, S., Singh, G., Saini, P.L., and Reddy, M.K., Tetrahedron Lett., 2014, vol. 55, p. 4657. doi 10.1016/j.tetlet.2014.06.068CrossRefGoogle Scholar
  19. 19.
    Posevins, D., Suta, K., and Turks, M., Eur. J. Org. Chem., 2016, vol. 7, p. 1414.CrossRefGoogle Scholar
  20. 20.
    Callens, E., Burton, A.J., and Barrett, A.G.M., Tetrahedron Lett., 2006, vol. 47, p. 8699.CrossRefGoogle Scholar
  21. 21.
    Firouzabadi, H., Iranpoor, N., and Khoshnood, A., Catal. Commun., 2007, vol. 9, p.529.CrossRefGoogle Scholar
  22. 22.
    Jefferies, L.R. and Cook, S.P., Tetrahedron, 2014, vol. 70, p. 4204.CrossRefGoogle Scholar
  23. 23.
    Khusnutdinov, R.I., Shchadneva, N.A., Mayakova, Yu.Yu., Khisamova, L.F., and Dzhemilev, U.M., Russ. J. Org. Chem., 2011, vol. 47, p. 1682. doi 10.1134/S1070428011110042CrossRefGoogle Scholar
  24. 24.
    Dzhemilev, U.M., Khusnutdinov, R.I., Shchadneva, N.A., and Khisamova, L.F., RF Patent no. 2448953, 2012.Google Scholar
  25. 25.
    Kalkhambkar, R.G., Waters, S.N., and Laali, K.K., Tetrahedron Lett., 2011, vol. 52, p. 867. doi 10.1016/j.tetlet.2010.12.028CrossRefGoogle Scholar
  26. 26.
    Jiang, F., Lin, Y.-J., Duan, H.-F., Li, Z.-H., Cao, J.-G., and Liang, D.-P., Chem. Res. Chin. Univ., 2010, vol. 26, p.384.Google Scholar
  27. 27.
    Pawar, D.M., Khalil, A.A., Hooks, D.R., Collins, K., Elliott, T., Stafford, J., Smith, L., and Noe, E.A., J. Am. Chem. Soc., 1998, vol. 120, p. 2108. doi 10.1021/ja9723848CrossRefGoogle Scholar
  28. 28.
    CrysAlisPrO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171.NET).Google Scholar
  29. 29.
    Sheldrick, G.M., Acta Cryst., Sect. A, 2008, vol. 64, p.112.CrossRefGoogle Scholar
  30. 30.
    Isaev, S.D., Novoselov, E.F., and Yurchenko, A.G., Zh. Org. Khim., 1985, vol. 21, p. 114.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • A. R. Bayguzina
    • 1
  • A. R. Lutfullina
    • 1
  • R. I. Khusnutdinov
    • 1
  1. 1.Institute of Petrochemistry and Catalysis of the Russian Academy of SciencesUfa, BashkortostanRussia

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