Abstract
Reaction of 1,5-diketones with 1,2-diamino-4-nitrobenzene gave a mixture of the 6- and 7-nitro derivatives of 4a,9-diaza-1,2,4a,9a-tetrahydrofluorene. Oxidation of the 6-nitro derivatives with MnO2 gives para-quinone imines with elimination of the nitro groups. Oxidation of the 7-nitro derivative and oxidative conjugation of 5-nitro-2,2-pentamethylene-1,2-dihydrobenzimidazole with primary amines in the presence of MnO2 gives nitro ortho-quinone imines.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
L. N. Donchak, A. N. Saverchenko, V. A. Kaminskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 7, 956 (1984).
V. A. Kaminskii, O. Yu. Slabko, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 6, 793 (1988).
V. A. Kaminskii, O. Yu. Slabko, S. é. Kraeva, and M. N. Tilichenko, Zh. Org. Khim., 24, 228 (1988).
O. Yu. Slabko, V. A. Kaminskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 11, 1500 (1989).
K. E. Davies, G. E. Domany, M. Farhat, J. A. Herbert, A. M. Jefferson, M. A. Martin, and H. Suschitzky, J. Chem. Soc., Perkin 1, No. 11, 2465 (1984).
R. Garner, G. V. Garner, and H. Suschitzky, J. Chem. Soc. C., No. 6, 825 (1970).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 927–930, July, 1990.
Rights and permissions
About this article
Cite this article
Kaminskii, V.A., Slabko, O.Y. & Gomolach, M.V. Reaction of 1,2-diamino-4-nitrobenzene with 1,5-diketones. Synthesis and oxidative reactions of nitrobenzimidazoles. Chem Heterocycl Compd 26, 772–775 (1990). https://doi.org/10.1007/BF00509705
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00509705