Abstract
The method of HPLC was used to investigate the influence of temperature, solvent, the nature of the nucleophile, and the type of v-acceptor on the rate of substitution of the nitro group in 4-nitroquinoline N-oxide by atoms of halogens. Convenient methods for the synthesis of 4-halo-substited quinoline N-oxides under conditions of activation of the reaction by Lewis and Bronsted-Lowry acids are proposed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. V. Ryzhakov and L. L. Rodina,Zh. Org. Khim.,30, 1417 (1994).
V. P. Andreev, E. G. Kalistratova, and A. V. Ryzhakov,Khim. Geterotsikl. Soedin., No. 4, 516 (1996).
G. Bekker,Introduction to the Electronic Theory of Organic Reactions [Russian translation], Mir, Moscow (1977), pp. 204, 504.
A. S. Dneprovskii and T. I. Temnikova,The Theoretical Fundamentals of Organic Chemistry [in Russian], Khimiya, St. Petersburg. (1979), pp. 319, 398.
E. Ochiai,Aromatic Amine Oxides, Elsevier, Amsterdam (1967), p. 373.
Additional information
Petrozavodsk State University, Pewtrozavodsk 185640, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1523–1527, November, 1999.
Rights and permissions
About this article
Cite this article
Andreev, V.P., Ryzhakov, A.V. Activation of nucleophilic substitution reactions in 4-nitroquinoline N-oxide by v-acceptors. Chem Heterocycl Compd 35, 1329–1333 (1999). https://doi.org/10.1007/BF02252003
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02252003