Advertisement

Russian Journal of General Chemistry

, Volume 88, Issue 2, pp 325–329 | Cite as

Synthesis of New Unsaturated Amines by The Stevens Rearrangement

  • M. O. Manukyan
  • A. Kh. Gyulnazaryan
  • A. V. Babakhanyan
  • A. A. Shahkhatuni
  • K. S. Barseghyan
Letters to the Editor
  • 59 Downloads

Abstract

Monoalkylation of 1,4-dichlorobut-2-ene with prop-2-yn-1-ol under phase-transfer catalysis conditions led to the formation of 1-(prop-2-yn-1-yloxy)-4-chlorobut-2-ene. The latter reacted with dimethylamine to afford N,N-dimethyl-4-(prop-2-yn-1-yloxy)but-2-enyl-1-amine. Its quaternization afforded new ammonium salts containing 4-(prop-2-yn-1-yloxy)but-2-enyl group. Unsaturated tertiary amines formed as a result of Stevens 3,2-rearrangement of quaternary salts.

Keywords

1-(prop-2-yn-1-yloxy)-4-chlorobut-2-ene N,N-dimethyl-4-(prop-2-yn-1-yloxy)but-2-enyl-1-amine Stevens 3,2-rearrangement unsaturated tertiary amines 

References

  1. 1.
    Okada, K. and Tanaka, M., J. Chem. Soc. Perkin Trans. 1, 2002, no. 23, p. 2704. doi 10.1039/B205588KCrossRefGoogle Scholar
  2. 2.
    Glaeske, K.W. and West, F.G., Org. Lett., 1999, vol. 1, p. 31. doi 10.1021/ol9905349CrossRefGoogle Scholar
  3. 3.
    Nitrogen, Oxygen and Sulfur Ylide Chemistry, Clark, J.S., Ed., Oxford: Oxford University Press, 2002.Google Scholar
  4. 4.
    Tayama, E., Nanbara, Sh., and Nakai, T., Chem. Lett., 2006, vol. 35, no. 5, p. 478. doi 10.1246/cl.2006.478.CrossRefGoogle Scholar
  5. 5.
    Sweeney, J.B., Tavassoli, A., and Workman, J.A., Tetrahedron, 2006, vol. 62, no. 49, p. 11506. doi 10.1016/i.tet.2006.06.043CrossRefGoogle Scholar
  6. 6.
    Workman, J.A., Garrido, N.P., Sançon, J., Roberts, E., Wessel, H.P., and Sweeney, J.B., J. Am. Chem. Soc., 2005, vol. 127, no. 4, p. 1066. doi 10.1021/ja043768CrossRefGoogle Scholar
  7. 7.
    Zhang J., Chen Z.-X., Du T., Li B., Gu Y., and Tian Sh.-K., Org. Lett., 2016, vol. 18, no. 19, p. 4872. doi 10.1021/acs.orglett.6b02344CrossRefGoogle Scholar
  8. 8.
    Kocharyan, S.T., Ogandzanyan, S.M., Razina, T.L., and Babayan, A.T., Zh. Org. Khim., 1982, vol. 18, no. 9, p. 1861.Google Scholar
  9. 9.
    Kocharyan, S.T., Ogandzanyan, S.M., and Babayan, A.T., Arm. Khim. Zh., 1976, vol. 29, no. 1, p. 42.Google Scholar
  10. 10.
    Babakhanyan, A.V., Gyul’nazaryan, A.Kh., Saakyan, T.A., Ovakimyan, S.A., Babayan, Zh.R., and Arutyunyan, R.S., Russ. J. Appl. Chem., 2001, vol. 74, no. 11, p. 1968. doi 10.1023/A:1014890005402CrossRefGoogle Scholar
  11. 11.
    Kaurai, H., Yabuhara, T., Shirai, A., Maeda, T., and Nagamune, H., Eur. J. Med. Chem., 2006, vol. 41, no. 1, p. 437. doi 10.1016/j.ejmech.2002.10.021CrossRefGoogle Scholar
  12. 12.
    Babakhanyan, A.V., Manukyan, M.O., Babayan, Zh.R., Aleksanyan, Yu.T., Margaryan, A.V., and Ghazaryan, A.E., Med. Nauka Armenii NAN RA, 2014, vol. 54, no. 1, p. 46.Google Scholar
  13. 13.
    Kinoyan, F.S., Khim. Zh. Arm., 2011, vol. 64, no. 4, p. 565.Google Scholar
  14. 14.
    Babayan, A.T., Chukhajyan, E.O., and Chukhajyan, El.O., Zh. Org. Khim., 1971, vol. 7, no. 3, p. 470.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • M. O. Manukyan
    • 1
  • A. Kh. Gyulnazaryan
    • 1
  • A. V. Babakhanyan
    • 2
  • A. A. Shahkhatuni
    • 3
  • K. S. Barseghyan
    • 1
  1. 1.Institute of Organic Chemistry of Scientific-Technological Center of Organic and Pharmaceutical ChemistryNational Academy of Sciences of ArmeniaYerevanArmenia
  2. 2.Armenian State Pedagogical University after Kh. AbovyanYerevanArmenia
  3. 3.Scientific-Technological Center of Organic and Pharmaceutical ChemistryNational Academy of Sciences of the Republic of ArmeniaYerevanArmenia

Personalised recommendations