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Reactions of Schiff bases with alkyl vinyl ethers

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Summary

  1. 1.

    Schiff bases react with alkyl vinyl ethers in presence of Lewis acids (BF3, AlCl3, AlBr3) by the diene synthesis scheme with formation of 4-alkoxy-2-aryl-1,2,3,4-tetrahydroquinolines.

  2. 2.

    Under the action of p-toluenesulfonic acid or of oxidizing agents 4-alkoxy-2-aryl-1,2,3,4-tetrahydroquinolines are converted into the corresponding 2-arylquinolines.

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Literature cited

  1. 1.

    L. S. Povarov and B. M. Mikhailov, Izv. AN SSSR. Otd. Khim. N.,1963, 55.

  2. 2.

    L. S. Povarov, V. I. Grigos, R. A. Karakhanov, and B. M. Mikhailov, Izv. AN SSSR. Ser. Khim.,1964, 179.

  3. 3.

    L. S. Povarov, V. I. Grigos, and B. M. Mikhailov, Izv. AN SSSR. Ser. Khim.,1963, 2039.

  4. 4.

    L. S. Povarov, V. I. Grigos, S. M. Shostakovskii, and B. M. Mikhailov, Izv. AN SSSR. Ser. Khim.,1965, 1891.

  5. 5.

    L. S. Povarov and B. M. Mikhailov, Izv. AN SSSR. Ser. Khim.,1955, 191.

  6. 6.

    R. Elderfield, Heterocyclic Compounds [Russian translation], IL, Moscow (1955), p. 191.

  7. 7.

    C. K. Ingold, Mechanism of Reactions and the Structure of Organic Compounds [Russian translation], Moscow (1959), p. 568.

  8. 8.

    A. S. Onishchenko, Diene Synthesis [in Russian], Izd. AN SSSR, Moscow (1963), p. 62.

  9. 9.

    C. Walling and H. J. Schugar, J. Amer. Chem. Soc.,85, 607 (1963).

  10. 10.

    Ya. K. Syrkin and I. I. Moiseev, Uspekhi Khimii,27, 1321 (1958).

  11. 11.

    M. G. Gonikberg, Zh. Fiz. Khimii,34, 225 (1960).

  12. 12.

    H. Henecka, Zeitschrift für Naturforschung,46, 15 (1949).

  13. 13.

    J. Sauer and H. Wiest, Angew. Chem.,74, 353 (1962).

  14. 14.

    G. Ya. Kondrat'eva and Huang ChÊng-hÊng, Dokl. AN SSSR,141, 861 (1961).

  15. 15.

    P. Brocklehurst, Tetrahedron,18, 299 (1962).

  16. 16.

    V. I. Minkin, Yu. A. Gidanov, and E. A. Medyantsev, Dokl. AN SSSR,159, 1330 (1964).

  17. 17.

    J. Mathieu and J. Valle, Uspekhi Khimii,28, 1216 (1959).

  18. 18.

    O. Doebner and W. V. Miller, Ber.,16, 1665 (1883).

  19. 19.

    J. Braun and L. Braun, Ber.,60, 1253 (1927).

  20. 20.

    N. N. Goldberg and R. Levine, J. Amer. Chem. Soc.,77, 3647 (1955).

  21. 21.

    O. Doebner, Liebigs Ann. Chem.,249, 106 (1888).

  22. 22.

    R. C. Elderfield, W. J. Gensler, T. H. Bembry, T. A. Williamson, and H. Weisl, J. Amer. Chem. Soc.,68, 1589 (1946).

  23. 23.

    O. Doebner and P. Kuntze, Liebigs Ann. Chem.,249, 133 (1888).

  24. 24.

    O. Doebner and P. Kuntze, Liebigs Ann. Chem.,249, 115 (1888).

  25. 25.

    O. Doebner, Liebigs Ann. Chem.,242, 287 (1887).

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Additional information

This article is published in accordance with a resolution of the Conference of Editors-in-Chief of Journals of the Academy of Sciences of the USSR of July 12, 1962, as a dissertation paper by V. I. Grigos.

Translated from Izvestiya Akademii Nauk SSSR, Khimicheskaya, No. 12, pp. 2163–2172, December, 1965

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Grigos, V.I., Povarov, L.S. & Mikhailov, B.M. Reactions of Schiff bases with alkyl vinyl ethers. Russ Chem Bull 14, 2129–2135 (1965). https://doi.org/10.1007/BF00846001

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Keywords

  • Ether
  • Vinyl
  • Diene
  • Schiff Base
  • Schiff