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Chemistry of Heterocyclic Compounds

, Volume 28, Issue 9, pp 1066–1069 | Cite as

Heteroadamantanes and their derivatives

18. Synthesis of derivatives of 1-phenyl-3,6-diazahomoadamantane with nitro and amino groups at the benzene ring and functional groups at the backbone C(9) atom
  • A. I. Kuznetsov
  • U. Barri
  • G. Mazhed
  • I. A. Vladimirova
Article

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.

Keywords

Sodium Aluminum Nitrate Potassium Nickel 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    A. I. Kuznetsov, I. A. Vladimirova, T. M. Serova, and A. S. Moskovkin, Khim. Geterotsikl. Soedin., No. 5, 653 (1992).Google Scholar
  2. 2.
    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).Google Scholar
  3. 3.
    N. S. Vul'fson (ed.), Preparative Organic Chemistry [in Russian], Gos. Nauch.-Tekhn. Izd. Khim. Lit., Moscow (1959), pp. 212, 226.Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • A. I. Kuznetsov
    • 1
  • U. Barri
    • 1
  • G. Mazhed
    • 1
  • I. A. Vladimirova
    • 1
  1. 1.M. V. Lomonosov Institute of Precision Chemical TechnologyMoscow

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