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Opening of the pyridine ring of compounds of the hydroxyquinoline series

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The nitrosation of 2-, 3-, and 4-hydroxyindoles was investigated. The Beckmann rearrangement with opening of the pyridine ring to form anthranilic acids or their derivatives occurs during the action of benzenesulfonyl chloride in alkaline media on 3-nitroso-4-hydroxycarbostyrils.

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Literature cited

  1. A. N. Kost and A. P. Stankevichus, Khim. Geterotsikl. Soedin., 1288 (1971).

  2. A. N. Kost, A. P. Stankevichus, and L. N. Zhukauskaite, Khim. Geterotsikl, Soedin., 504 (1971).

  3. E. Koenigs and J. Freund, Ber., 74, 1085 (1941).

    Google Scholar 

  4. R. E. Bowman, A. Campbell, and E. M. Tanner, J. Chem. Soc., 444 (1959).

  5. J. A. Bosson, M. Rasmussen, E. Ritchie, A. V. Robertson, and W. C. Taylor, Austral. J. Chem., 16, 480 (1963).

    Google Scholar 

  6. M. Boetius, E. Carstens, and C. Meyer, German Patent No. 13,870 (1957); Chem. Abstr., 53, 11,415 (1959).

    Google Scholar 

  7. E. Ziegler and K. Gelfert, Monatsh., 90, 822 (1959).

    Google Scholar 

  8. Organic Synthesis (Russian translation], Vol. 4, Inostr. Lit., Moscow (1953), pp. 320, 592.

  9. Synthesis of Heterocyclic Compounds [in Russian], Vol. 5, Erevan (1960), p. 39.

  10. General Practicum in Organic Chemistry [in Russian], Moscow (1965), pp. 185, 596.

  11. R. E. Lutz, J. F. Codington, R. J. Rowlett, A. J. Deinet, and P. S. Bailey, J. Am. Chem. Soc., 68, 1810 (1946).

    Google Scholar 

  12. A. Lefeuvre, Mem. Mus. Nat. Hist. Natur. (Paris), Ser. D, Sci. Phys.-Chim., 3(4), 58 (1966); Chem. Abstr., 69, 35,898 (1968).

    Google Scholar 

  13. E. H. Huntress and J. Bornstein, J. Am. Chem. Soc., 71, 745 (1949).

    Google Scholar 

  14. J. A. Lamberton and J. R. Price, Austral. J. Chem., 6, 173 (1953).

    Google Scholar 

  15. B. Pawlewski, Ber., 38, 1683 (1905).

    Google Scholar 

  16. R. Willstäter and W. Kahn, Ber., 37, 405 (1904).

    Google Scholar 

  17. J. Houben and W. Brassert, Ber., 39, 3238 (1906).

    Google Scholar 

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Authors and Affiliations

  1. Kaunas Medical Institute, M. V. Lomonosov Moscow State University, USSR

    A. N. Kost, L. N. Zhukauskaite & A. P. Stankevichus

Authors
  1. A. N. Kost
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  2. L. N. Zhukauskaite
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  3. A. P. Stankevichus
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Additional information

Communication VII of the series “Nitrosophenols and Their Rearrangement Products.” See [1] for communication VI.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1214–1217, September, 1971.

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Kost, A.N., Zhukauskaite, L.N. & Stankevichus, A.P. Opening of the pyridine ring of compounds of the hydroxyquinoline series. Chem Heterocycl Compd 7, 1141–1144 (1971). https://doi.org/10.1007/BF00510023

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  • DOI: https://doi.org/10.1007/BF00510023

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