Abstract
2-Methoxy- and 2-hydroxy-substituted quinoxaline and pyrazine N,N′-dioxides and N-oxides of a number of quinoxaline-2-carboxylic acid derivatives were synthesized in order to study their biological activity. It is shown that the N-monoxides and N,N′-dioxides of 2-hydroxy derivatives of quinoxaline exist primarily in the oxo form. Strong intramolecular hydrogen bonds were detected in the case of 1-N-oxides of 2-hydroxy and 2-carboxamido derivatives of quinoxaline. Substances with antibacterial and antituberculous activity were found among the synthesized compounds.
Similar content being viewed by others
Literature cited
K. G. Cunningham, G. T. Newbold, F. S. Spring, and J. Stark, J. Chem. Soc., 2091 (1949).
A. S. Elina and E. N. Padeiskaya, Proceedings of the S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry Institute, Moscow, No. 2 [in Russian], Moscow (1971), p. 197.
W. A. Lott and E. Shaw, J. Amer. Chem. Soc., 71, 70 (1949).
A. S. Elina, Zh. Obshch. Khim., 34, 2809 (1964).
A. S. Elina, E. N. Padeiskaya, O. Yu. Magidson, G. N. Pershin, K. A. Belozerova, and V. I. Fatneva, USSR Author's Certificate No. 320,495 (1970); Byul. Izobr., No. 34 (1972).
B. Klein, E. O'Donnel, and J. M. Gordon, J. Org. Chem., 29, 2623 (1964).
L. Bernardi, G. Palamidessi, A. Leone, and G. Larini, Gazz. Chim. Ital., 91, 1431 (1961); Chem. Abstr., 57, 2223e (1962).
S. Okada, A. Kosasayama, T. Konno, and F. Uchimaru, Chem. Pharm. Bull., 19, 1337 (1971); Ref. Zh. Khim., 3Zh439 (1972).
A. S. Elina, Zh. Obshch. Khim., 32, 2956 (1962).
J. K. Landquist, J. Chem. Soc., 2830 (1953).
A. S. Elina, T. N. Zykova, O. Yu. Magidson, G. N. Pershin, L. G. Tsyrul'nikova, and V. I. Fatneva, USSR Author's Certificate No. 235767 (1967); Byul. Izobr., No. 2, 204 (1970).
A. S. Elina and O. Yu. Magidson, Zh. Obshch. Khim., 25, 161 (1955).
A. S. Elina, I. S. Musatova, and L. G. Tsyrul'nikova, Khim.-Farmats. Zh., No. 8, 6 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 278–283, February, 1976.
Rights and permissions
About this article
Cite this article
Elina, A.S., Musatova, I.S., Peresleni, E.M. et al. Synthesis, structure, and biological properties of N-oxides of some 2-substituted quinoxalines and pyrazines. Chem Heterocycl Compd 12, 239–244 (1976). https://doi.org/10.1007/BF00523980
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00523980