Abstract
A study has been made of the alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline by alkyl halides in the presence of inorganic bases. New methods for the synthesis of 1-substituted 2-oxo-3-carbethoxy-4-ihydroxyquinolines are examined.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
I. V. Ukrainets, P. A. Bezugly [Bezuglyi], S. G. Taran, O. V. Gorokhova, and A. V. Turov, Tetrahedron Lett.,36, 7747 (1995).
I. V. Ukrainets, P. A. Bezuglyi, O. V. Gorokhova, V. I. Treskach, and A. V. Turov, Khim. Geterotsikl. Soedin., No. 1, 105 (1993).
I. V. Ukrainets, S. G. Taran, P. A. Bezuglyi, S. N. Kovalenko, A. V. Turov, and N. A. Marusenko, Khim. Geterotsikl. Soedin., No. 9, 1223 (1993).
I. V. Ukrainets, O. V. Gorokhova, S. G. Taran, P. A. Bezuglyi, N. I. Filimonova, and A. V. Turov, Khim. Geterotsikl. Soedin., No. 10, 1400 (1994).
I. V. Ukrainets, S. G. Taran, O. A. Evtifeeva, and A. V. Turov, Khim. Geterotsikl. Soedin., No. 8, 1101 (1993).
I. V. Ukrainets, O. V. Gorokhova, S. G. Taran, and A. V. Turov, Khim. Geterotsikl. Soedin., No. 10, 1397 (1994).
I. V. Ukrainets, O. V. Gorokhova, S. G. Taran, P. A. Bezuglyi, A. V. Turov, N. A. Marusenko, and O. A. Evtifeeva, Khim. Geterotsikl. Soedin., No. 7, 958 (1994).
M. M. Girges, M. A. Hanna, H. M. Hassan, and E. B. Moawad, Collect. Czech. Chem. Commun.,53, 179 (1988).
R. E. Lutz, G. Ashburn, J. A. Freek, R. N. Jordan, N. H. Leake, T. A. Martin, R. J. Rowlett, and J. W. Wilson, J. Am. Chem. Soc.,68, 1285 (1946).
G. R. Proctor, W. J. Ross, and A. Tapia, J. Chem. Soc., Perkin Trans. 1, No. 8, 1803 (1972).
I. V. Ukrainets, P. A. Bezuglyi, O. V. Gorokhova, V. I. Treskach, V. A. Georgiyants, S. V. Slobodzyan, Khar'kov State Pharmaceutical Institute, Khar'kov (1990); paper filed at UkrNIINTI, 12/5/90, No. 1966-Uk90.
Halil Hosgoren and Giray Topal, Turk. Kim. Derg.,14, 303 (1990).
A. E. Agronomov and Yu. S. Shabarov, Laboratory Operations in Organic Laboratory Course [in Russian], Khimiya, Moscow (1974), p. 75.
A. F. Pozharskii, Theoretical Principles of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).
A. F. Pozharskii and A. T. Soldatenkov, Signet-Ring Molecules [in Russian], Khimiya, Moscow (1993).
I. V. Ukrainets, S. G. Taran, O. V. Gorokhova, N. A. Marusenko, S. N. Kovalenko, A. V. Turov, N. I. Filimonova, and S. M. Ivkov, Khim. Geterotsikl. Soedin., No. 2, 195 (1995).
M. Dewar, E. Zoebisch, F. Healy, and J. Stewart, J. Am. Chem. Soc.,107, 3902 (1985).
U. Burket and N. L. Allinger, Molecular Mechanics, American Chemical Society, Washington, D. C. (1986), p. 386.
I. Hermecz, Z. Meszaros, and K. Simon, J. Chem. Soc., Perkin Trans. 1, No. 8, 1795 (1984).
M. Ramesh and P. Shanmugam, Indian J. Chem. B,24, 602 (1985).
G. C. Hopkins, J. Jonak, H. Tieckelmann, and J. Minnemeyer, J. Org. Chem.,31, 3969 (1966).
Hui-Yuan Guo, Lan-Ying Sun, Yi-Cheng Cao, Zhi-Ming Tian, and Zhi-Ping Zhang, Chinese J. Pharm.,22, No 8, 339 (1991).
R. K. Mackie and D. M. Smith, Guidebook to Organic Synthesis, Longman, New York (1982).
Additional information
For communication 29, see [1].
Ukrainian Pharmaceutical Academy, Khar'kov 310002. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1104–1112, August, 1996. Original article submitted June 10, 1996.
Rights and permissions
About this article
Cite this article
Ukrainets, I.V., Taran, S.G., Gorokhova, O.V. et al. 4-Hydroxy-2-quinolones. 30 Alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline. Chem Heterocycl Compd 32, 952–959 (1996). https://doi.org/10.1007/BF01176973
Issue Date:
DOI: https://doi.org/10.1007/BF01176973