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.
Similar content being viewed by others
Literature cited
A. N. Kost and A. P. Stankevichus, Khim. Geterotsikl. Soedin., 1288 (1971).
A. N. Kost, A. P. Stankevichus, and L. N. Zhukauskaite, Khim. Geterotsikl, Soedin., 504 (1971).
E. Koenigs and J. Freund, Ber., 74, 1085 (1941).
R. E. Bowman, A. Campbell, and E. M. Tanner, J. Chem. Soc., 444 (1959).
J. A. Bosson, M. Rasmussen, E. Ritchie, A. V. Robertson, and W. C. Taylor, Austral. J. Chem., 16, 480 (1963).
M. Boetius, E. Carstens, and C. Meyer, German Patent No. 13,870 (1957); Chem. Abstr., 53, 11,415 (1959).
E. Ziegler and K. Gelfert, Monatsh., 90, 822 (1959).
Organic Synthesis (Russian translation], Vol. 4, Inostr. Lit., Moscow (1953), pp. 320, 592.
Synthesis of Heterocyclic Compounds [in Russian], Vol. 5, Erevan (1960), p. 39.
General Practicum in Organic Chemistry [in Russian], Moscow (1965), pp. 185, 596.
R. E. Lutz, J. F. Codington, R. J. Rowlett, A. J. Deinet, and P. S. Bailey, J. Am. Chem. Soc., 68, 1810 (1946).
A. Lefeuvre, Mem. Mus. Nat. Hist. Natur. (Paris), Ser. D, Sci. Phys.-Chim., 3(4), 58 (1966); Chem. Abstr., 69, 35,898 (1968).
E. H. Huntress and J. Bornstein, J. Am. Chem. Soc., 71, 745 (1949).
J. A. Lamberton and J. R. Price, Austral. J. Chem., 6, 173 (1953).
B. Pawlewski, Ber., 38, 1683 (1905).
R. Willstäter and W. Kahn, Ber., 37, 405 (1904).
J. Houben and W. Brassert, Ber., 39, 3238 (1906).
Author information
Authors and Affiliations
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.
Rights and permissions
About this article
Cite this article
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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00510023