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
  • 31 Downloads

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 

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References

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    A. I. Kuznetsov, I. A. Vladimirova, T. M. Serova, and A. S. Moskovkin, Khim. Geterotsikl. Soedin., No. 5, 653 (1992).Google Scholar
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    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
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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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