Chemistry of Heterocyclic Compounds

, Volume 53, Issue 9, pp 1045–1049 | Cite as

Iminothiolactone-thiolactam rearrangement in the synthesis of 4-amino-6-thioxo-3,7,9-triazatricyclo-[,5]undec-4-ene-2,10-diones

  • Sergey V. FedoseevEmail author
  • Mikhail Yu. Belikov
  • Oleg V. Ershov
  • Victor A. Tafeenko

The reaction of 4-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with Lawesson's reagent proceeded as an iminothiolactone-thiolactam rearrangement, leading to the formation of 4-amino-6-thioxo-3,7,9-triazatricyclo[,5]undec-4-ene-2,10-diones.


iminothiolactone Lawesson's reagent spiroheterocycles sulfur heterocycles thiolactam rearrangement 


The study was performed within the framework of scholarship SP-2802.2015.4 awarded by the President of the Russian Federation to young scientists and graduate students.

The X-ray structural studies were performed by using equipment of the Chair of General Chemistry, Faculty of Chemistry, M. V. Lomonosov Moscow State University.

Supplementary material

10593_2017_2167_MOESM1_ESM.pdf (1.1 mb)
ESM 1 (PDF 1089 kb)


  1. 1.
    Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523.CrossRefGoogle Scholar
  2. 2.
    Tejedor, D.; Méndez-Abt, G.; Cotos, L.; García-Tellado, F. Chem. Soc. Rev. 2013, 42, 458.CrossRefGoogle Scholar
  3. 3.
    Métro, T.-X.; Duthion, B.; Pardo, D. G.; Cossy, J. Chem. Soc. Rev. 2010, 39, 89.CrossRefGoogle Scholar
  4. 4.
    Gómez, A. M.; Lobo, F.; Uriel, C.; López J. C. Eur. J. Org. Chem. 2013, 32, 7221.CrossRefGoogle Scholar
  5. 5.
    Tabolin, A. A.; Ioffe, S. L. Chem. Rev. 2014, 114, 5426.CrossRefGoogle Scholar
  6. 6.
    Snape, T. J. Chem. Soc. Rev. 2008, 37, 2452.CrossRefGoogle Scholar
  7. 7.
    Kayukov, Ya. S.; Bardasov, I. N.; Karpov, S. V.; Ershov, O. V.; Nasakin, O. E.; Kayukova, O. V.; Tafeenko, V. A. Russ. J. Org. Chem. 2012, 48, 1447. [Zh. Org. Khim. 2012, 48, 1463.]Google Scholar
  8. 8.
    Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Nasakin, O. E.; Tafeenko, V. A. Tetrahedron Lett. 2014, 55, 2730.CrossRefGoogle Scholar
  9. 9.
    Han, Y.; Tang, W.-Q.; Guo, L.-Y.; Yan, C.-G. Tetrahedron 2014, 70, 6663.CrossRefGoogle Scholar
  10. 10.
    Angelin, M.; Vongvilai, P.; Fischera, A.; Ramström, O. Chem. Commun. 2008, 768.Google Scholar
  11. 11.
    Song, Y. S.; Lee, C. H.; Lee, K.-J. J. Heterocycl. Chem. 2003, 40, 939.CrossRefGoogle Scholar
  12. 12.
    Palombi, L.; Molab, A. D.; Massa, A. New J. Chem. 2015, 39, 81.CrossRefGoogle Scholar
  13. 13.
    Wu, X.-F.; Oschatz, S.; Block, A.; Spannenbergb, A.; Langer, P. Org. Biomol. Chem. 2014, 12, 1865.Google Scholar
  14. 14.
    Ghozlan, S. A. S.; Abdelmoniem, D. M.; Mady, M. F.; Abdelmoniem, A. M.; Abdelhamid, I. A. Heterocycles 2016, 92, 637.CrossRefGoogle Scholar
  15. 15.
    Hilmy, K. M. H.; Soliman, D. H.; Shahin, E. B. A.; El-Deeb, H. S.; El-Kousy, S. M. Eur. J. Med. Chem. 2014, 78, 419.CrossRefGoogle Scholar
  16. 16.
    Briel, D.; Aurich, R.; Egerland, U.; Unverferth, K. Pharmazie 2005, 60(10), 732.Google Scholar
  17. 17.
    Fathalla, W. M.; Pazdera P. Molecules. 2002, 7, 96.CrossRefGoogle Scholar
  18. 18.
    Karlivan, G. A.; Valter, R. E.; Bace, A. E. Chem. Heterocycl. Compd. 1999, 35, 866. [Khim. Geterotsikl. Soedin. 1999, 988.]Google Scholar
  19. 19.
    Kambe, T.; Maruyama, T.; Nagase, T.; Ogawa, S.; Minamoto, Ch.; Sakata, K.; Maruyama, T.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2012, 20, 702.CrossRefGoogle Scholar
  20. 20.
    Luo, W.; Yu, Q.-Sh.; Salcedo, I.; Holloway, H. W.; Lahiri, D. K.; Brossi, A.; Tweedie, D.; Greig, N. H. Bioorg. Med. Chem. 2011, 19, 3965.CrossRefGoogle Scholar
  21. 21.
    Orzesko, A.; Vilpo, J.; Kaminska, B. Pharmazie 2003, 58, 169.Google Scholar
  22. 22.
    Di Pardo, R. M.; Patane, M. A.; Newton, R. C.; Price, R. A.; Broten, T. P.; Chang, R. S. L.; Ransom, R. W.; Di Salvo, J.; Freidinger, R. M.; Bock, M. G. Bioorg. Med. Chem. Lett. 2001, 11, 1959.Google Scholar
  23. 23.
    Fedoseev, S. V.; Ershov, O. V.; Belikov, M. Yu.; Lipin, K. V.; Bardasov, I. N.; Nasakin, O. E.; Tafeenko, V. A. Tetrahedron Lett. 2013, 54, 2143.CrossRefGoogle Scholar
  24. 24.
    Fedoseev, S. V.; Ershov, O. V.; Lipin, K. V.; Belikov, M. Yu. RSC Adv. 2016, 6, 10597.CrossRefGoogle Scholar
  25. 25.
    Fedoseev, S. V.; Lipin, K. V.; Ershov, O. V.; Belikov, M. Yu.; Tafeenko, V. A. Russ. J. Org. Chem. 2016, 52, 1606. [Zh. Org. Khim. 2016, 52, 1613.]Google Scholar
  26. 26.
    Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210.Google Scholar
  27. 27.
    Belikov, M. Yu.; Belikova, I. V.; Ershov, O. V.; Fedoseev, S. V. Russ. J. Org. Chem. 2016, 52, 1854. [Zh. Org. Khim. 2016, 52, 1860.]Google Scholar
  28. 28.
    Eremkin, A. V.; Ershov, O. V.; Davydova, V. V.; Nasakin, O. E. Russ. J. Org. Chem. 2015, 51, 1813. [Zh. Org. Khim. 2015, 51, 1846.]Google Scholar
  29. 29.
    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.Google Scholar
  30. 30.
    Brandenburg, K. DIAMOND, Release 2.1d; Crystal Impact GbR: Bonn, 2000.Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • Sergey V. Fedoseev
    • 1
    Email author
  • Mikhail Yu. Belikov
    • 1
  • Oleg V. Ershov
    • 1
  • Victor A. Tafeenko
    • 2
  1. 1.Chuvash State University named after I. N. UlyanovCheboksaryRussia
  2. 2.M. V. Lomonosov Moscow State UniversityMoscowRussia

Personalised recommendations