Chemistry of Heterocyclic Compounds

, Volume 34, Issue 8, pp 971–975 | Cite as

Reaction of 6-methyl-2-methylthio-3-(2-thioxo-1,3,4-oxadiazol-5-yl)methyl-4(3H)-pyrimidinone with amines

  • V. Yakubkene
  • P. Vainilavichyus


The reaction of 6-methyl-2-methylthio-3-(2-thioxo-1,3,4-oxadiazol-5-yl)methyl-4(3H)-pyrimidinone with butyland benzylamine and also with piperidine and morpholine has been studied. It was found that the primary amines not only open the 1,3,4-oxadiazole ring to form the corresponding thiosemicarbazides but also substitute the methylthio group at position 2 in the pyrimidine ring. Morpholine can only open the 1,3,4-oxadiazole ring but piperidine can also substitute the methythio group to give an oxadiazolethione piperidinium salt.


Organic Chemistry Pyrimidine Piperidine Primary Amine Morpholine 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    D. H. Boschelli, D. T. Connor, D. A. Bornemeier, R. D. Dyer, J. A. Kennedy, P. J. Kuipers, G. C. Okonkwo, D. J. Schrier, and C. D. Wright, J. Med. Chem.,36, 1802 (1993).CrossRefGoogle Scholar
  2. 2.
    A. S. Avakyan, S. O. Vartanyan, É. A. Markaryan, O. M. Martirosyan, and O. M. Avakyan, Khim.-Farm. Zh., No. 6, 683 (1988).Google Scholar
  3. 3.
    R. Kalsi, K. Pande, and J. P. Barthwal, Indian J. Chem., Sect. B,27B, 197 (1988).Google Scholar
  4. 4.
    I. P. Singh, A. K. Saxena, and K. Shankar, Eur, J. Med. Chem. Chim. Ther.,21, 267 (1986).Google Scholar
  5. 5.
    R. S. Varma, A. Shuhla, and R. K. Chatterjee, Indian J. Chem., Sect. B,32B, 697 (1993).Google Scholar
  6. 6.
    R. Nigam, S. Swarup, V. K. Saxena, and H. K. Singh, J. Indian Chem. Soc.,69, 692 (1992).Google Scholar
  7. 7.
    S. Saxena, M. Verma, A. K. Saxena, and K. Shankar, Indian J. Pharm. Sci.,117, 184259 (1992).Google Scholar
  8. 8.
    A. Tantavy and A. E. M. Barghash, Alexandria J. Pharm. Sci.,2, 50 (1988).Google Scholar
  9. 9.
    S. Yamamoto, Jpn. Patent 05124948, Chem. Abstr.,119, 146370 (1993).Google Scholar
  10. 10.
    F. Bettarini, L. Capuzzi, P. La Porta, S. Massimini, and V. Caprioli, European Patent 533276, Chem. Abstr.,119, 49400 (1993).Google Scholar
  11. 11.
    D. H. Boschelli, D. T. Connor, C. R. Kostlan, J. B. Kramer, M. D. Mullican, and J. Ch. Sircar, European Patent 449211, Chem. Abstr.,116, 6570 (1992).Google Scholar
  12. 12.
    T. R. Belliotti, D. T. Connor, and C. R. Kostlan, PCT Int., World Patent WO9213844, Chem. Abstr.,118, 6990 (1993).Google Scholar
  13. 13.
    W. Eckhardt, E. Beriger, and H. Zondler, European Patent 371925, Chem. Abstr.,113, 191385 (1990).Google Scholar
  14. 14.
    C. Ainswort, J. Am. Chem. Soc.,78, 4475 (1956).Google Scholar
  15. 15.
    G. Myakushkene, P. Vainilavichyus, A. Gettsgaim, and R. Shematovich, Khim. Geterotsikl. Soedin., No. 5, 770 (1993).Google Scholar
  16. 16.
    D. A. Charistos, G. V. Vagenas, L. C. Tzavellas, C. A. Tsoleridis, and N. A. Rodios, J. Heterocyclioc Chem.,31, 1593 (1994).Google Scholar
  17. 17.
    J. Imai, J. Makromol. Chem.,83, 170 (1965).Google Scholar
  18. 18.
    V. I. Kelarev, G. V. Shvekhgeimer, and A. F. Lunin, Khim. Geterotsikl. Soedin., No. 9, 1271 (1984).Google Scholar
  19. 19.
    P. Vainilavichyus, V. Syadyaryavichyute, and S. Motsishkite, Khim. Geterotsikl. Soedin., No. 12, 1655 (1992).Google Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • V. Yakubkene
  • P. Vainilavichyus

There are no affiliations available

Personalised recommendations