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Pd-Cu-catalyzed synthesis of N-(2E,4)- and N-(2Z,4)-enyne cyclic amines

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Abstract

By Pd-Cu-catalyzed coupling of (2E)- and (2Z)-3-chloroprop-2-en-1-ylamines and alkynes a stereoselective method of the synthesis was developed for a series of (2E,4)- and (2Z,4)-enyne cyclic amines.

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References

  1. Sukamoto, S., Takahashi, M., Matsunaga, S., Fusetani, N., and Van Soest, R.W., J. Nat. Prod., 2000, vol. 63, p. 682.

    Article  Google Scholar 

  2. Nussbaumer, P., Leitner, I., Mraz, K., and Stutz, A., J. Med. Chem., 1995, vol. 38, p. 1831.

    Article  CAS  Google Scholar 

  3. Alami, M., Ferri, F., and Gaslain, Y., Tetrahedron Lett., 1996, vol. 37, p. 57.

    Article  CAS  Google Scholar 

  4. Lhermitte, H. and Grierson, D.S., Contemp. Org. Synth., 1996, vol. 3, p. 41.

    Article  CAS  Google Scholar 

  5. Lhermitte, H. and Grierson, D.S., Contemp. Org. Synth., 1996, vol. 3, p. 93.

    Article  CAS  Google Scholar 

  6. Zein, N., Sinha, A.M., McGahren, W.J., and Ellestad, G.A., Science, 1988, vol. 240, p. 1198.

    Article  CAS  Google Scholar 

  7. Fiandanese, V., Bottalico, D., Marchese, G., and Punzi, A.. Tetrahedron., 2004, vol. 60, p. 11421.

    Article  CAS  Google Scholar 

  8. Zou, Y., Millar, J.G. Tetrahedron Lett., 2010, vol. 51, p. 1336.

    Article  CAS  Google Scholar 

  9. El-Jaber, N., Estevez-Braun, A., Ravelo, A.G., Munoz-Munoz, O., Rodriguez-Afonso, A., and Murguia, J.R., J. Nat. Prod., 2003, vol. 66, p. 722.

    Article  CAS  Google Scholar 

  10. Fontana, A., d’Ippolito, G., d’Souza, L., Mollo, E., Parames-waram, P.S., and Cimino, G., J. Nat. Prod., 2001, vol. 64, p. 131.

    Article  CAS  Google Scholar 

  11. Nicolaou, K.C. and Dai, W.M., Angew. Chem., Int. Ed., 1991, vol. 30, p. 1387.

    Article  Google Scholar 

  12. Gunawardena, J.W., Klingberg, G.U., and Huang, D., Tetrahedron, 1996, vol. 52, p. 6453.

    Article  Google Scholar 

  13. Gung, B.W. and Kumi, G., J. Org. Chem., 2004, vol. 69, p. 3488.

    Article  CAS  Google Scholar 

  14. Kumar, P., Naidu, S.V., and Gupta, P., J. Org. Chem., 2005, vol. 70, p. 2843.

    Article  CAS  Google Scholar 

  15. Crousse, B., Mladenova, M., Ducept, P., Alami, M., and Linstrumelle, G., Tetrahedron, 1999, vol. 55, p. 4353.

    Article  CAS  Google Scholar 

  16. Casey, C.P. and Strotman, N.A., J. Org. Chem., 2005, vol. 70, p. 2576.

    Article  CAS  Google Scholar 

  17. Saito, S. and Yamamoto, Y., Chem. Rev., 2000, vol. 100, p. 2901.

    Article  CAS  Google Scholar 

  18. Sonogashira, K., Tokai, Y., and Hagihara, N., Tetrahedron Lett., 1975, vol. 16, p. 4467.

    Article  Google Scholar 

  19. Chinchilla, R. and Najera, C., Chem. Rev., 2007, vol. 107, p. 874.

    Article  CAS  Google Scholar 

  20. Negishi, E.I. and Anastasia, L., Chem. Rev., 2003, vol. 103, p. 1979.

    Article  CAS  Google Scholar 

  21. Sunagatullina, A.Sh., Shakhmaev, R.N., and Zorin, V.V., Zh. Obshch. Khim., 2012, vol. 82, p. 1216.

    Google Scholar 

  22. Handbook of Organopalladium Chemistry for Organic Synthesis, Negishi, E., Ed., New York: Wiley Intersci., 2002, vol. 1, p. 1659.

    Google Scholar 

  23. Alami, M. and Linstrumelle, G., Tetrahedron Lett., 1991, vol. 32, p. 6109.

    Article  CAS  Google Scholar 

  24. Alami, M., Crousse, B., and Ferri, F., J. Organometal. Chem., 2001, vol. 624, p. 114.

    Article  CAS  Google Scholar 

  25. Takhautdinova, A.U., Mindiyarova, E.R., Shakhmaev, R.N., and Zorin, V.V., Zh. Prikl. Khim., 2011, vol. 84, p. 513.

    Google Scholar 

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Authors and Affiliations

  1. Ufa State Petroleum Technological University, Ufa, 450062, Russia

    A. Sh. Sunagatullina, R. N. Shakhmaev & V. V. Zorin

Authors
  1. A. Sh. Sunagatullina
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  2. R. N. Shakhmaev
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  3. V. V. Zorin
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Correspondence to A. Sh. Sunagatullina.

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Original English Text © A.Sh. Sunagatullina, R.N. Shakhmaev, V.V. Zorin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 5, pp. 747–750.

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Sunagatullina, A.S., Shakhmaev, R.N. & Zorin, V.V. Pd-Cu-catalyzed synthesis of N-(2E,4)- and N-(2Z,4)-enyne cyclic amines. Russ J Org Chem 49, 730–733 (2013). https://doi.org/10.1134/S1070428013050163

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  • DOI: https://doi.org/10.1134/S1070428013050163

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