Abstract
Acetamides that contain acceptor substituents in the α position react with quinox-alinium salts to give cis-hexahydropyrrolo[2,3-b]quinoxalin-2-ones. Acetic acid arylamides are inert under these conditions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
M. G. Ponizovskii, O. N. Chupakhin, V. N. Charushin, and G. G. Aleksandrov, Khim. Geterotsikl. Soedin., No. 10, 1410 (1982).
E. Matsumura, M. Ariga, and Y. Tohda, Bull. Chem. Soc. Jpn., 53, 2891 (1980).
E. Matsumura and M. Ariga, Bull. Chem. Soc. Jpn., 46, 3144 (1973).
Y. C. Tong and H. O. Kerlinger, in: Proceedings of the 8th International Congress of Heterocyclic Chemistry (1981), p. 30.
A. Albert and H. Mizuno, J. Chem. Soc., Perkin I, No. 15, 1615 (1973).
V. N. Charushin, O. N. Chupakhin, and A. I. Rezvukhin, Heterocycles, 16, 196 (1981).
O. N. Chupakhin, V. N. Charushin, N. A. Klyuev, A. I. Rezvukhin, and V. A. Semion, Khim. Geterotsikl. Soedin., No. 10, 1392 (1981).
V. N. Charushin, M. G. Ponizovskii, O. N. Chupakhin, A. I. Rezvukhin, G. M. Petrova, and Yu. A. Efremov, Khim. Geterotsikl. Soedin., No. 11, 1543 (1981).
K. Hirota, Y. Kitade, S. Senda, M. J. Halat, K. A. Watanabe, and J. J. Fox, J. Am. Chem. Soc., 101, 4423 (1979).
K. Hirota, Y. Kitade, and S. Senda, Tetrahedron Lett., No. 22, 2409 (1981).
G. O. Torosyan, G. G. Gekchyan, G. A. Panosyan, R. T. Grigoryan, and A. T. Babayan, Zh. Org. Khim., 18, 1413 (1982).
J. Klicnar, M. Haiec, J. Hoffmann, and M. Veĉera, Collect. Czech. Chem. Commun., 36, 262 (1971).
Q. Ahmed, T. Wagner-Jauregg, E. Pretsch, and J. Seibe, Helv. Chim. Acta, 56, 1646 (1973).
J. W. Bunting and M. G. Meathrel, Can. J. Chem., 50, 919 (1972).
M. Karplus, J. Am. Chem. Soc., 85, 2870 (1963).
K. L. Williamson and W. S. Johnson, J. Am. Chem. Soc., 83, 4623 (1961).
O. N. Chupakhin, V. N. Charushin, L. M. Naumova, and A. I. Rezvukhin, Dokl. Akad. Nauk SSSR, 261, 384 (1981).
S. J. Jan, W. H. Burton, Phing-Lu-Chin, and C. C. Cheng, J. Heterocycl. Chem., 15, 297 (1978).
Organic Syntheses [Russian translation], Collective Vol. 3, Inostr. Lit., Moscow (1952), p. 73.
Author information
Authors and Affiliations
Additional information
See [1] for communication 6.
Translated from Khimiya Geterosiklicheskikh Soedinenii, No. 8, pp. 1120–1124, August, 1983.
Rights and permissions
About this article
Cite this article
Charushin, V.N., Naumova, L.M., Izmailova, G.G. et al. Cyclization of N-alkylazinium cations with bisnucleophiles. 7. Reactions of quinoxalinium salts with α-substituted acetamides. Chem Heterocycl Compd 19, 901–905 (1983). https://doi.org/10.1007/BF00516461
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00516461