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Chemistry of Heterocyclic Compounds

, Volume 16, Issue 11, pp 1171–1175 | Cite as

Synthesis of analogs of 5(4)-aminoimidazole-4(5)-carboxamide and purines. 9. peculiarities of the reaction of 5(4)-aminoimidazole-4(5)-carboxhydrazide with nitrous acid and of 5-diazoimidazole-4-carboxazide with amines

  • V. S. Mokrushin
  • I. S. Selezneva
  • V. I. Nifontov
  • Z. V. Pushkareva
Article

Abstract

The reaction of 5(4)-aminoimidazole-4(5)-carboxhydrazide with nitrous acid was investigated. A mixture of four compounds, viz., 5-diazoimidazole-4-carboxazide, 5-diazoimidazole-4-carboxylic acid, 5(4)-aminoimidazole-4(5)-carboxazide, and 2-azahypoxanthine, is formed under all of the investigated conditions, 5(4)-Azidoimidazole-4(5)-carboxamide derivatives were obtained in the reaction of diazoimidazole-carboxazide with various amines in protic and aprotic solvents. 5-N-(Piperidyl)-azoimidazole-4-carboxazide was isolated only in the reaction with piperidine in an aqueous medium.

Keywords

Organic Chemistry Nitrous Acid Aqueous Medium Purine Piperidine 
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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Literature cited

  1. 1.
    V. I. Nifontov, I. S. Selezneva, V. S. Mokrushin, Z. V. Pushkareva, and V. A. Trofimov, Khim. Geterotsikl. Soedin., No. 7, 984 (1979).Google Scholar
  2. 2.
    Y. F. Shealy, R. F. Struck, L. B. Holun, and J. A. Montgomery, J, Org. Chem., 26, 2396 (1961).Google Scholar
  3. 3.
    Y. F. Shealy, J. Pharm. Sci., 59, 1533 (1970).Google Scholar
  4. 4.
    V. I. Ofitserov, Z. V. Pushkareva, V. S. Mokrushin, and K. V. Aglitskaya, Khim. Geterotsikl. Soedin., No. 9, 1292 (1973).Google Scholar
  5. 5.
    M. Debeljak-Sustar, V. Stanovnik, M, Tishler, and Z. Zrimsek, J, Org. Chem., 43, 393 (1978).Google Scholar
  6. 6.
    G. Heller and A. Siller, J. Prakt. Chem., 116, 9 (1927).Google Scholar
  7. 7.
    R. A. Long, J. F. Gester, and L. B. Townsend, J. Heterocycl. Chem., No. 7, 863 (1970).Google Scholar
  8. 8.
    Y. F. Shealy, C. A. Krauth, and J. A. Montgomery, J. Org. Chem., 27, 2150 (1962).Google Scholar
  9. 9.
    V. I. Nifontov, V. S. Mokrushin, Z. V. Pushkareva, and A. A. Mukhina, Khim. Geterotsikl. Soedin., No. 1, 94 (1973).Google Scholar
  10. 10.
    Y. F. Shealy and C. Allen O'Dell, J. Heterocycl. Chem., 10, 839 (1974).Google Scholar

Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • V. S. Mokrushin
    • 1
  • I. S. Selezneva
    • 1
  • V. I. Nifontov
    • 1
  • Z. V. Pushkareva
    • 1
  1. 1.S. M. Kirov Ural Polytechnic InstituteSverdlovsk

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