Two methods of preparation have been proposed and the synthesis has been effected of a large series of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. The possibility of using various condensing agents for converting them into the corresponding 1,3,4-oxa-diazoloquinolines has been studied. Results are given of an investigation of the antitubercular activity of the synthesized compounds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. Ukrainets, A. A. Tkach, and I. O. Pankratov, Khim. Geterotsikl. Soedin., 1189 (2008). [Chem. Heterocycl. Comp., 44, 956 (2008)].
G. I. Zhungietu and V. G. Granik, Basic Principles in the Construction of Drugs [in Russian], State University Publishing Polygraphic Complex of Moldova University, Kishinev (2000).
I. V. Ukrainets, Jaradat Nidal Amin, P. A. Bezuglyi, O. V. Gorokhova, and L. V. Sidorenko, Visnyk Farmatsii, No. 1 (21), 13 (2000).
I. V. Ukrainets, O. S. Prokopenko, L. V. Sidorenko, and O. V. Gorokhova, Visnyk Farmatsii, No. 3 (39), 3 (2004).
I. V. Ukrainets, L. V. Sidorenko, O. S. Prokopenko, V. B. Rybakov, and V. V. Chernyshev, Zh. Org. Farm. Khim., 2, Issue 4 (8), 17 (2004).
J. Hill, in: A. R. Katritzky and C. W. Rees (editors), Comprehensive Heterocyclic Chemistry on CD-ROM: 7-Volume Set, Vol. 6, Elsevier, Oxford (1997), p. 440.
C. G. Overberger, J.-P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen-Nitrogen Bonds, The Roland Press Co, New York, 1966.
F. T. Coppo, K. A. Evans, T. L. Graybill, and G. Burton, Tetrahedron Lett., 45, 3257 (2004).
I. R. Baxendale, S. V. Ley, and M. Martinelli, Tetrahedron, 61, 5323 (2005).
J. Y. Hwang, H.-S. Choi, D.-H. Lee, and Y.-D. Gong, J. Comb. Chem., 7, 816 (2005).
H. A. Rajapakse, H. Zhu, M. B. Young, and B. Mott, Tetrahedron Lett., 47, 4827 (2006).
D. H. R. Barton and W. D. Ollis (editors), Comprehensive Organic Chemistry, Pergamon, Oxford (1979). Russian translation: Vol. 9, Khimiya, Moscow (1985), p. 524.
I. V. Ukrainets, E. A. Taran, O. V. Gorokhova, Jaradat Nidal Amin, L. N. Voronina, and I. V. Porokhnyak, Khim. Geterotsikl. Soedin., 409 (2000). [Chem. Heterocycl. Comp., 36, 346 (2000)].
I. V. Ukrainets, P. A. Bezuglyi, V. I. Treskach, M. Yu. Kornilov, A. V. Turov, A. I. Maslennikov, S. V. Gradchenko, and V. I. Krivobok, Khim. Geterotsikl. Soedin., 1086 (1992). [Chem. Heterocycl. Comp., 28, 912 (1992)].
I. V. Ukrainets, L. V. Sidorenko, S. V. Slobodzyan, V. B. Rybakov, and V. V. Chernyshev, Khim. Geterotsikl. Soedin., 1362 (2005). [Chem. Heterocycl. Comp., 41, 1158 (2005)].
V. N. Baumer, O. V. Shishkin, I. V. Ukrainets, L. V. Sidorenko, and S. A. El Kayal, Acta Crystallogr., E60, o2356 (2004).
Author information
Authors and Affiliations
Corresponding author
Additional information
* For Communication 148 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1655–1663, November, 2008.
Rights and permissions
About this article
Cite this article
Ukrainets, I.V., Tkach, A.A. & Yang, L.Y. 4-hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids. Chem Heterocycl Comp 44, 1347–1354 (2008). https://doi.org/10.1007/s10593-009-0198-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-009-0198-6