Advertisement

Chemistry of Heterocyclic Compounds

, Volume 49, Issue 7, pp 1097–1101 | Cite as

Synthesis of New Imidazo[4,5-e][1,3]thiazolo-[3,2-b][1,2,4]triazine Derivatives

  • G. A. Gazieva
  • S. A. Serkov
  • N. V. Sigai
  • N. N. Kostikova
  • Yu. V. Nelyubina
  • E. A. Shishkova
  • A. N. Kravchenko
Article

Previously unknown (Z)-6-aryl(hetaryl)methylidene derivatives of imidazo[4,5-e][1,3]thiazolo[3,2-b]-[1,2,4]triazine-2,7-diones were synthesized by aldol-crotonic condensation of imidazo[4,5-e]-[1,3]thiazolo[3,2-b][1,2,4]triazine-2,7-diones with aromatic or heteroaromatic aldehydes, or by three-component condensation of imidazo[4,5-e][1,2,4]triazine-3-thione, bromoacetic acid, and aldehyde.

Keywords

aromatic and heteroaromatic aldehydes imidazo[4,5-e][1,3]thiazolo[3,2-b][1,2,4]triazine-2,7-diones perhydroimidazo[4,5-e][1,2,4]triazine-3-thione aldol-crotonic condensation one-pot condensation 

References

  1. 1.
    M. N. Nasr, M. M. Gineinah, and E. R. El-Bendary, Arch. Pharm., 336, 560 (2003).CrossRefGoogle Scholar
  2. 2.
    S. N. Sriharsha, S. Satish, S. Shashikanth, and K. A. Raveesha, Bioorg. Med. Chem., 14, 7476 (2006).CrossRefGoogle Scholar
  3. 3.
    I. R. Siddiqui, P.K. Singh, J. Singh, and J. Singh, J. Agric. Food Chem., 51, 7062 (2003).CrossRefGoogle Scholar
  4. 4.
    V. Gududuru, E. Hurh, J. T. Dalton, and D. D. Miller, Bioorg. Med. Chem. Lett., 14, 5289 (2004).CrossRefGoogle Scholar
  5. 5.
    R. Ottanà, S. Carotti, R. Maccari, I. Landani, G. Chiricosta, B. Caciagli. M. G. Vigorita, and E. Mini, Bioorg. Med. Chem. Lett., 15, 3930 (2005).Google Scholar
  6. 6.
    J. Balzarini, B. Orzeszko-Krzesińska, J. K. Maurin, and A. Orzeszko, Eur. J. Med. Chem., 44, 303 (2009).CrossRefGoogle Scholar
  7. 7.
    J. P. Devlin and K. D. Hargrave, Tetrahedron, 45, 4327 (1989).CrossRefGoogle Scholar
  8. 8.
    W. K. P. Amery and J. P. M. Bruynseels, Int. J. Immunopharmacol., 14, 481 (1992).CrossRefGoogle Scholar
  9. 9.
    D. I. Trepanier and P. E. Krieger, US Pat. Appl. 3641019.Google Scholar
  10. 10.
    R. M. Abdel-Rahman, M. Seada, M. Fawzy, and I. El-Baz, Boll. Chim. Farm.,133, 381 (1994).Google Scholar
  11. 11.
    R. M. Abdel-Rahman, M. Seada, M. Fawzy, and I. El-Baz, Pharmazie, 49, 729 (1994).Google Scholar
  12. 12.
    H. Zhou, S. Wu, S. Zhai, A. Liu, Y. Sun, R. Li, Y. Zhang, S. Ekins, P. W. Swaan, B. Fang, B. Zhang, and B. Yan, J. Med. Chem., 51, 1242 (2008).CrossRefGoogle Scholar
  13. 13.
    M. E. Jung, J.-M. Ku, L. Du, H. Hu, and R. A. Gatti, Bioorg. Med. Chem. Lett., 21, 5842 (2011).CrossRefGoogle Scholar
  14. 14.
    M. Mushtaque, F. Avecilla, and A. Azam, Eur. J. Med. Chem., 55, 439 (2012).CrossRefGoogle Scholar
  15. 15.
    S. V. Vasilevskii, P. A. Belyakov, G. A. Gazieva, Yu. V. Nelyubina, N. G. Kolotyrkina, and A. N. Kravchenko, Mendeleev. Commun., 20, 47 (2010).CrossRefGoogle Scholar
  16. 16.
    G. A. Gazieva, P. A. Poluboyarov, Yu. V. Nelyubina, M. I. Struchkova, and A. N. Kravchenko, Khim. Geterotsiklich. Soed., 1483 (2012). [Chem. Heterocycl. Compd., 48, 1382 (2012)].Google Scholar
  17. 17.
    R. Ottanà, R. Maccari, M. L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocrea, M. G. Vigorita, and E. Mini, Bioorg. Med. Chem., 13, 4243 (2005).CrossRefGoogle Scholar
  18. 18.
    O. Bozdağ-Dundar, Ö. Özgen, A. Menteşe, N. Altanlar, O. Atli, E. Kendi, and R. Ertan, Bioorg. Med. Chem., 15, 6012 (2007).CrossRefGoogle Scholar
  19. 19.
    R. Lesyk, O. Vladzimirska, S. Holota, L. Zaprutko, and A. Gzella, Eur. J. Med. Chem., 42, 641 (2007).CrossRefGoogle Scholar
  20. 20.
    S. V. Vasilevskii, Yu. V. Nelyubina, N. G. Kolotyrkina, P. A. Belyakov, L. B. Kulikova, and A. N. Kravchenko, Mendeleev. Commun., 20, 288 (2010).CrossRefGoogle Scholar
  21. 21.
    S. A. Sigachev, A. N. Kravchenko, K. A. Lyssenko, P. A. Belyakov, O. V. Lebedev, and N. N. Makhova, Mendeleev. Commun., 13, 190 (2003).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • G. A. Gazieva
    • 1
  • S. A. Serkov
    • 1
  • N. V. Sigai
    • 1
  • N. N. Kostikova
    • 1
  • Yu. V. Nelyubina
    • 2
  • E. A. Shishkova
    • 1
  • A. N. Kravchenko
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsMoscowRussia

Personalised recommendations