Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with nucleophiles
- 94 Downloads
Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with aliphatic amines and sodium hydroxide resulted in removal of one N-oxide oxygen atom and formation of 4-alkylamino- or 4-hydroxy-substituted 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1-oxides, respectively. The title compound reacted with ammonia and methylamine in the presence of MnO2 with conservation of both N-oxide moieties, and the products were 4-amino- and 4-methylamino-5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxides. The reactions with aromatic amines were accompanied by removal of both N-oxide oxygen atoms with formation of N-aryl-5-nitrospiro[benzimidazole-2,1′-cyclohexane]-4-amines. In the reactions of 5-nitrospiro-[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with sodium azide and aromatic amine hydrochlorides nucleophilic replacement of the 5-nitro group by azido or arylamino occurred, in the first case both N-oxide fragments being conserved. The reactions with aromatic amine hydrochlorides afforded N-aryl-5-nitrospiro[benzimidazole-2,1′-cyclohexan]-4-amine 1-oxides. Treatment of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with sodium cyanide led to the formation of 5-oxo-3,5-dihydrospiro[benzimidazole-2,1′-cyclohexane]-4-carbonitrile 1-oxide.
KeywordsCyclohexane Benzimidazole Aromatic Amine Sodium Cyanide Aniline Hydrochloride
Unable to display preview. Download preview PDF.
- 1.Suschitzky, H., Croat. Chim. Acta, 1986, vol. 59, p. 57.Google Scholar
- 2.Brian, I., Bull. Soc. Chim. Belg., 1990, vol. 99, p. 673.Google Scholar
- 3.Latham, D.W.S., Meth-Cohn, O., Suschitzky, H., and Herbert, J.A.L., J. Chem. Soc., Perkin Trans. 1, 1977, p. 470.Google Scholar
- 7.Samsonov, V.A., Volodarskii, L.B., and Shamirzaeva, O.V., Khim. Geterotsikl. Soedin., 1994, p. 524.Google Scholar
- 8.Samsonov, V.A. and Volodarskii, L.B., Zh. Org. Khim., 1982, vol. 18, p. 656.Google Scholar
- 10.Samsonov, V.A., Bagryanskaya, I.Yu., Gatilov, Yu.V., and Savel’ev, V.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2011, p. 1697.Google Scholar
- 12.Davies, K.E., Domany, G.E., Farhat, M., Herbert, J.A.L., Jefferson, A.M., Martin, M.A.G., and Suschitzky, H., J. Chem. Soc., Perkin Trans. 1, 1984, p. 2465.Google Scholar
- 13.Gorelik, M.V. and Gladysheva, T.Kh., Zh. Org. Khim., 1977, vol. 13, p. 1958.Google Scholar