Chemistry of Heterocyclic Compounds

, Volume 5, Issue 3, pp 398–399 | Cite as

Intramolecular rearrangements

III. The rearrangement of S-aminoalkyl derivatives of 2-mercaptopyrimidine and 2-mercapto-4,6-diaminopyrimidine
  • L. V. Pavlova
  • F. Yu. Rachinskii


It has been shown that S-β-aminoalkyl derivatives of 2-mercaptopyrimidine and 2-mercapto-4, 6-diaminopyrimidine, containing primary and secondary amino groups, undergo S → N rearrangement in neutral or weakly alkaline solution, with the formation of the corresponding aminothiols. In the case of derivatives of 2-mercapto-4, 6-diaminopyrimidine, however, the S → N rearrangement proceeds more slowly, apparently as a result of the difficulty of formation of the intermediate cyclic compound.


Organic Chemistry Alkaline Solution Weakly Alkaline Cyclic Compound Secondary Amino 
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.


  1. 1.
    J. Khym, R. Shapira, and D. Doherty, J. Am. Chem. Soc., 79, 5663, 1957.Google Scholar
  2. 2.
    J. Khym, D. Doherty, and R. Shapira, J. Am. Chem. Soc., 80, 3342, 1958.Google Scholar
  3. 3.
    D. Doherty and R. Shapira, J. Org. Chem., 28, 1939, 1963.Google Scholar
  4. 4.
    F. Yu. Rachinskii, A. S. Mozzhukin, N. M. Slavacheskaya, and L. L. Tank, Usp. khim., 28, 1488, 1959.Google Scholar
  5. 5.
    L. V. Pavlova and F. Yu. Rachinskii, ZhOKh, 35, 493, 1965.Google Scholar
  6. 6.
    Shih-Hsi-Chu and H. Mautner, J. Org. Chem., 27, 2899, 1962.Google Scholar
  7. 7.
    R. Clapp, L. Long, and T. Hasselstrom, J. Org. Chem., 26, 1666, 1961.Google Scholar
  8. 8.
    R. Clapp, L. Long, and T. Hasselstrom, J. Org. Chem., 28, 1308, 1963.Google Scholar
  9. 9.
    L. V. Pavlova, and F. Yu. Rachinskii, ZhOKh, collection: Biologically Active Compounds [in Russian], 186, 1965.Google Scholar
  10. 10.
    T. Johnston and A. Gallagher, J. Org. Chem., 28, 1305, 1963.Google Scholar
  11. 11.
    Kh. L. Muravich-Aleksandr, A. V. El'tsov, and M. B. Kolesova, collection: The Synthesis of Natural Compounds and Their Analogs and Fragments [in Russian], Nauka, Moscow-Leningrad, 251, 1965.Google Scholar
  12. 12.
    B. Hunt, J. McOmie, and E. Sayer, J. Chem. Soc., 525, 1959.Google Scholar
  13. 13.
    V. Berezovskii and A. Yurkevich, ZhOKh, 32, 1655, 1962.Google Scholar
  14. 14.
    The Synthesis of Organic Compounds, Vol. 2 [in Russian], IL, Moscow, 40, 1949.Google Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • L. V. Pavlova
    • 1
  • F. Yu. Rachinskii
    • 1
  1. 1.Kirov Academy of Military MedicineLeningrad

Personalised recommendations