Abstract
Wolff—Kishner reduction of the keto group of 3,6-diazahomoadamantan-9-ones to a methylene group was investigated. It was shown that diazahomoadamantanones yield hydrazones in the reaction with hydrazine hydrate, and they are converted into 3,6-diazahomoadamantane derivatives with one or two substituents in nodal positions when heated with a base. Unsubstituted 3,6-diazahomoadamantane is not formed in these conditions, since 3,6-diazahomoadamantan-9-one hydrazone is convened into azine when heated above 70‡C. Other hydrazones are also converted into azines when heated, but at a higher temperature —above 150‡C.
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A. I. Kuznetsov, T. D. Sokolova, I. A. Vladimirova, T. M. Serova, M. Yu. D'yakov, L. A. Shundrin, A. S. Moskovkin, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 5, 648 (1992).
A. I. Kuznetsov and I. A. Vladimirova, Khim. Geterotsikl. Soedin., No. 12, 1700 (1988).
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).
A. I. Kuznetsov, E. B. Basargin, M. Kh. Ba, A. S. Moskovkin, I. V. Miroshnichenko, and M. Ya. Botnikov, Khim. Geterotsikl. Soedin., No. 5, 647 (1989).
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See [1] for Communication 16.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 653–657, May, 1992.
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Kuznetsov, A.I., Vladimirova, I.A., Serova, T.M. et al. Heteroadamantanes and their derivatives. 17. Wolff—Kishner reduction of 3,6-diazahomoadamantan-9-ones. Chem Heterocycl Compd 28, 551–555 (1992). https://doi.org/10.1007/BF00475255
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DOI: https://doi.org/10.1007/BF00475255