Abstract
1-p-nitrophenyl-3,6-diazahomoadamantane and 1-p-nitrophenyl-3,6-diazahomoadamantan-9-one were obtained by nitration of 1-phenyl-3,6-diazahomoadamantane and 1-phenyl-3,6-diazahomoadamantan-9-one with a mixture of potassium nitrate and sulfuric acid; 1-p-nitrophenyl-3,6-diazahomoadamantan-9-one was reduced with sodium borohydride to 1-p-nitrophenyl-3,6-diazahomoadamantan-9-ol. It was found that the nitro groups of these nitrophenyldiazahomoadamantanes were reduced to amino groups by heating with hydrazine hydrate without a catalyst. 1-p-Aminophenyl-3,6-diazahomoadamantan-9-one was obtained by reduction of nitrophenyl-azahomoadamantanone with tin in sulfuric acid, and 9-amino-1-p-aminophenyl-3,6-diazahomo-adamantane was obtained by reduction of its oxime with a nickel—aluminum alloy in water—base medium.
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References
A. I. Kuznetsov, I. A. Vladimirova, T. M. Serova, and A. S. Moskovkin, Khim. Geterotsikl. Soedin., No. 5, 653 (1992).
A. I. Kuznetsov, I. A. Vladimirova, E. B. Basargin, M. Kh. Ba, A. S. Moskovkin, and M. Ya. Botnikov, Khim. Geterotsikl. Soedin., No. 5, 675 (1990).
N. S. Vul'fson (ed.), Preparative Organic Chemistry [in Russian], Gos. Nauch.-Tekhn. Izd. Khim. Lit., Moscow (1959), pp. 212, 226.
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See [1] for 17.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1257–1261, September, 1992.