Abstract
Ethyl ester derivatives of 6- and 8-substituted 2-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids have been synthesized by treatment of the diethyl ester of acetylmalonic acid with 2- or 4-substituted anilines. Condensation of these newly synthesized quinolinecarboxylic acid derivatives with 4-nitrobenzaldehyde resulted in the formation of 6- and 8-substituted 2-[2-(4-nitrophenyl)-vinyl]-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acids and ethyl esters of 6- and 8-substituted 2-[2-(4-nitrophenyl)vinyl]-4-acetoxy-3-quinolinecarboxylic acids. The tautomeric and conformational transformations of these newly synthesized compounds have also been investigated, using IR, NMR, and UV spectroscopy.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
R. G. Gould and W. A. Jacobs, J. Am. Chem. Soc.,61, 2890 (1939).
German Patent No. 2,705,446; A. Allais, F. Clemance, R. D. Deraedt, and O. Le Martret, Chem. Abstr.,87, 152042 (1976).
N. M. Sukhova, T. V. Lapina, and M. Yu. Lidak, Khim. Geterotsikl. Soedin., No. 11, 1521 (1983).
B. P. Bangdiwala and G. M. Desai, J. Indian Chem. Soc.,31, 553 (1954).
J. Egri, J. Halmos, and J. Rakoczi, Acta Chem. (Budapest),78, 217 (1973).
R. T. Coutts and D. G. Wibberley, J. Chem. Soc., No. 7, 2518 (1962).
A. Hideo, M. Tohru, J. Akio, K. Toshiaki, and N. Takenari, J. Med. Chem.,20, 791 (1977).
I. D. London and I. Wellings, J. Chem. Soc., No. 9, 3470 (1960).
I. D. London and G. Tennant, ibid., No. 8, 3092 (1962).
R. P. Staiger and E. B. Miller, J. Org. Chem.324, 1214 (1959).
R. Camps, Chem. Ber.,34, 2703 (1901).
Japanese Patent No. 7894; Y. Isowa, C. A.,67, 43561 (1967).
Japanese Patent No. 17168; Y. Isowa, C. A.,70, 57178 (1969).
L. I. Kononov, G. A. Veinberg, and é. Lukevits, Uzv. Akad. Nauk Latvian SSR, Ser. Khim., No. 5, 624 (1984).
V. A. Voronova and V. Kauss, Abstracts of Proceedings, Conference of Young Chemistry Students, Riga (1977), p. 14.
W. Borsche, W. Doeller, and M. Wagner-Roemmich, Chem. Ber.,76B, 1099 (1943).
I. Elguero, C. Marzin, A. R. Katritzky, and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York (1976).
I. T. Kay and P. I. Taylor, J. Chem. Soc., C, No. 21, 2656 (1968).
M. S. Onalli, M. Vaultier, and R. Carrie, Tetrahedron,36, 1812 (1980).
G. M. Coppola, A. D. Kahle, and M. I. Shapiro, Org. Magn. Reson.,17, 242 (1981).
J. M. Hearn, R. A. Morton, and J. C. E. Simpson, J. Chem. Soc., No. 12, 3318 (1951).
E. A. Fehnel, I. A. Deyrup, and M. B. Davidson, J. Org. Chem.,23, 1996 (1958).
A. Iiro, U. Shozo, and N. Haruki, Chem. Pharm. Bull.,129, 3712 (1981).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 931–938, July, 1988.
Rights and permissions
About this article
Cite this article
Kononov, L.I., Veinberg, G.A., Liepin'sh, É.É. et al. Synthesis and isomeric conversions of several 2-substituted 1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivatives. Chem Heterocycl Compd 24, 765–771 (1988). https://doi.org/10.1007/BF00633172
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00633172