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Investigation of the Fischer cyclization of diarylhydrazones and related secondary hydrazones

II. New examples of the effect of the structure of the aryl group on the orientation during rearrangement

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It was established by the method of intramolecular competition during the formation of an indole ring from N,N-diarylhydrazones in acidic media that aryl groups with p-ethoxycarbonyl or m-methoxy groups are less reactive than unsubstituted phenol, whereas the 2-naphthyl group is more reactive than the phenyl group. The results are examined from the point of view of the qualitative classification of the substituents with respect to their electronic effects.

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Literature cited

  1. V. A. Zagorevskii, N. F. Kucherova, N. M. Sharkova, T. I. Ivanova, and S. M. Klyuev, Khim. Geterotsikl. Soedin., No. 10, 1353 (1975).

    Google Scholar 

  2. L. N. Yakhontov, Usp. Khim., 37, 1258 (1968).

    Google Scholar 

  3. R. H. C. Elgersma, Enige Aspecten van de Indoolsynthese volgens Fischer, Rotterdam (1969).

  4. K. H. Pausacker and C. I. Schubert, J. Chem. Soc., 1814 (1950).

  5. J. McLean, S. McLean, and R. I. Reed, J. Chem. Soc., 2519 (1955).

  6. P. I. T. Scheltus, Kinetic Investigation of the Fischer Indole Synthesis, Leiden (1959).

  7. V. A. Zagorevskii, V. L. Savel'ev, and N. V. Dudykina, Zh. Org. Khim., 4, 2041 (1968).

    Google Scholar 

  8. V. A. Zagorevskii, V. L. Savel'ev, and L. M. Meshcheryakova, Khim. Geterotsikl. Soedin., No. 2, 1019 (1970).

    Google Scholar 

  9. N. M. Przheval'skii and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 11, 1581 (1974).

    Google Scholar 

  10. H. Ishii, T. Hagiwara, T. Ishikawa, and N. Ikeda, Heterocycles, No. 3, 75 (1975).

    Google Scholar 

  11. Farbenfabriken Bayer A.-G., British Patent No. 721171 (1954); Chem. Abstr., 50, 2685 (1956).

    Google Scholar 

  12. L. Kricka and J. Vernon, Can. J. Chem., 52, 299 (1974).

    Google Scholar 

  13. P. Schiss and A. Grieder, Helv. Chim. Acta, 57, 2643 (1974).

    Google Scholar 

  14. L. N. Yakhontov and E. V. Pronina, Zh. Org. Khim., 4, 1675 (1968).

    Google Scholar 

  15. I. I. Grandberg and V. I. Sorokin, Usp. Khim., 43, 266 (1974).

    Google Scholar 

  16. K. Ingold, Theoretical Foundations of Organic Chemistry [Russian translation], Mir, Moscow. (1973).

    Google Scholar 

  17. H. H. Stroh and G. Westphal, Chem. Ber., 96, 184 (1963).

    Google Scholar 

  18. R. F. Khadson, Usp. Khim., 45, 416 (1976).

    Google Scholar 

  19. G. A. Olah, K. Dunne, D. P. Kelly, and Y. K. Mo, J. Am. Chem. Soc., 94, 7438 (1972).

    Google Scholar 

  20. H. L. Goering and R. R. Jacobson, J. Am. Chem. Soc., 80, 3277 (1958).

    Google Scholar 

  21. G. Zahl, W. Kosbahn, and G. Kresze, Ann., No. 10, 1733 (1975).

    Google Scholar 

  22. B. Robinson, Usp. Khim., 40, 1434 (1971).

    Google Scholar 

  23. U. Widmer, J. Zsindely, H. J. Hansen, and H. Schmid, Helv. Chim. Acta, 56, 75 (1973).

    Google Scholar 

  24. D. A. Evans and A. M. Golob, J. Am. Chem. Soc., 97, 4765 (1975).

    Google Scholar 

  25. I. Heidt, E. Gombos, and F. Tudos, Kozlemen., 14, 183 (1966); Chem. Abstr., 66, 18552g (1967).

    Google Scholar 

  26. G. Palazzo and L. Baiocchii, Ann. Chim. (Rome), 55, 935 (1965).

    Google Scholar 

  27. I. R. Chalmers, H. T. Openschaw, and G. F. Smith, J. Chem. Soc., 1115 (1957).

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See [1] for communication I.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1072–1078, August, 1977.

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Zagorevskii, V.A., Kucherova, N.F. & Sharkova, N.M. Investigation of the Fischer cyclization of diarylhydrazones and related secondary hydrazones. Chem Heterocycl Compd 13, 862–867 (1977). https://doi.org/10.1007/BF00488911

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  • DOI: https://doi.org/10.1007/BF00488911

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