Abstract
It has been established that the cyclization of β-(2-carboxy-3-naphthylamino)propionic acid into N-acetyl-4-oxo-1, 2, 3, 4-tetrahydrobenzo[g]quinoline takes place with the participation of acetic anhydride and an alkali metal acetate. In the absence of the alkali metal acetate cyclization takes place in a different direction. A mechanism for this reaction has been proposed as taking place through the formation of an internal mixed anhydride, which decomposes under the reaction conditions into N-acetyl-4-oxo-1, 2, 3, 4-tetrahydrobenzo[g]-quinoline and carbon dioxide.
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A. F. Bekhli, N. P. Kozyreva, and N. P. Kostyuchenko, KhGS [Chemistry of Heterocyclic Compounds], 6, 71, 1970.
A. F. Bekhli and N. P. Kozyreva, KhGS [Chemistry of Heterocyclic Compounds], collection 1, 296, 1967.
German patent no. 287803; C., 86, II, 1034, 1915.
R. E. Lutz, J. F. Codington, R. J. Rowlett, A. J. Deinet, and R. S. Bailey, J. Am. Chem. Soc., 68, 1810, 1946.
A. F. Bekhli, E. M. Peresleni, and K. F. Turchin, KhGS [Chemistry of Heterocyclic Compounds], 6, 1970 (in press).
S. F. Mason, J. Chem. Soc., 4879, 1957.
G. M. Sukhotina, Dissertation: Studies in the Field of 4-Hydroxypyridone [in Russian], Moscow, 1966.
A. F. Bekhli, KhGS [Chemistry of Heterocyclic Compounds], 6, 65, 1970.
M. G. Blanc, Bull. Soc. chim. France, 3, 778, 1908.
F. C. Uhle, C. M. McEwen, H. Schröter, C. Juan, and B. W. Baker, J. Am. Chem. Soc., 82, 1200, 1960.
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For part V, see [1].
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Bekhli, A.F., Kozyreva, N.P. & Peresleni, E.M. Synthesis of benzo[g]quinoline derivatives. Chem Heterocycl Compd 6, 366–369 (1970). https://doi.org/10.1007/BF00471243
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DOI: https://doi.org/10.1007/BF00471243