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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 12, pp 1748–1755 | Cite as

Ethyl 2-Aminothiophene-3-Carboxylates in the Synthesis of Isomeric Thienopyridines

  • N. T. PokhodyloEmail author
  • O. Ya. Shyyka
  • N. D. Obushak
Article

A convenient method for the synthesis of thieno[3,2-c]pyridinones was developed. A number of thiophene derivatives was prepared, and the possibility of using thiophene desamino derivatives for the design of potentially biologically active molecules was demonstrated.

Keywords

aminothiophenes thienopyridinones thiophene-3-carboxylic acids Curtius rearrangement electrophilic cyclization 

References

  1. 1.
    Y. Huang and A. Doemling, Mol. Diversity, 15, 3 (2011).CrossRefGoogle Scholar
  2. 2.
    S. A. Al-Trawneh, M. M. El-Abadelah, J. A. Zahra, S. A. Al-Taweel, F. Zani, M. Incerti, A. Cavazzoni, and P. Vicini, Bioorg. Med. Chem., 19, 2541 (2011).CrossRefGoogle Scholar
  3. 3.
    N. I. Sweidan, M. Z. Nazer, M. M. El-Abadelah, and W. Voelter, Lett. Org. Chem., 7, 79 (2010).CrossRefGoogle Scholar
  4. 4.
    D. S. Dhanoa, O. Becker, S. Noiman, P. Mohanty, D. Chen, M. Lobera, L. Wu, Y. Marantz, B. Inbal, A. Heifetz, S. Bar-Haim, and S. Shacham, US Pat. Appl. 7982040.Google Scholar
  5. 5.
    J. W. Scott, B. J. W. van Denderen, S. B. Jorgensen, J. E. Honeyman, G. R. Steinberg, J. S. Oakhill, T. J. Iseli, A. Koay, P. R. Gooley, D. Stapleton, and B. E. Kemp, Chem. Biol., 15, 1220 (2008).CrossRefGoogle Scholar
  6. 6.
    G. Gentile, G. Bernasconi, A. Pozzan, G. Merlo, P. Marzorati, P. Bamborough, B. Bax, A. Bridges, C. Brough, P. Carter, G. Cutler, M. Neu, and M. Takada, Bioorg. Med. Chem. Lett., 15, 4823 (2011).CrossRefGoogle Scholar
  7. 7.
    J. Sircar, K. C. Sunil Kumar, T. J. Davis, and W. Ying, US Pat. Appl. 7365200.Google Scholar
  8. 8.
    K. Gewald, E. Schinke, and H. Bottcher, Chem. Ber., 99, 94 (1966).CrossRefGoogle Scholar
  9. 9.
    V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, Chem. Heterocycl. Compd., 3, 789 (1967). [Khim. Geterotsikl. Soedin., 1010 (1967).]CrossRefGoogle Scholar
  10. 10.
    J. Sice, J. Org. Chem., 19, 70 (1954).CrossRefGoogle Scholar
  11. 11.
    F. Bohlmann and E. Bresinsky, Chem. Ber., 97, 2109 (1964).CrossRefGoogle Scholar
  12. 12.
    T. L. Fevig, W. G. Phillips, and P. H. Lau, J. Org. Chem., 66, 2493 (2001).CrossRefGoogle Scholar
  13. 13.
    T. L. Fevig, P. H. Lau, and W. G. Phillips, EP Pat. Appl. 1023283.Google Scholar
  14. 14.
    N. Charrier, Z. Liu, and S. Z. Zard, Org. Lett., 14, 2018 (2012).CrossRefGoogle Scholar
  15. 15.
    N. Briet, M. H. Brookes, R. J. Davenport, F. C. A. Galvin, P. J. Gilbert, S. R. Mack, and V. Sabin, Tetrahedron, 58, 29, 5761 (2002).CrossRefGoogle Scholar
  16. 16.
    A. T. Mavrova, D. Wesselinova, Y. A. Tsenov, and P. Denkova, Eur. J. Med. Chem., 44, 63 (2009).CrossRefGoogle Scholar
  17. 17.
    T. Kohara, H. Tanaka, K. Kimura, H. Horiuchi, K. Seio, M. Arita, T. Fujimoto, and I. Yamamoto, J. Heterocycl. Chem., 39, 163 (2002).CrossRefGoogle Scholar
  18. 18.
    D. Melandri, P. C. Montevecchi, and M. L. Navacchia, Tetrahedron, 55, 12227 (1999).CrossRefGoogle Scholar
  19. 19.
    M. Susumu, T. Tatsuo, H. Tsunetoshi, H. Yoshiharu, O. Toshihiko, H. Hiroshi, K. Shiro, I. Masanao, A. Akinori, Y. Kiyoshi, and A. Fujio, J. Med. Chem., 46, 2446 (2003).CrossRefGoogle Scholar
  20. 20.
    A. Schöning and W. Friedrichsen, Liebigs Ann. Chem., 405 (1989).Google Scholar
  21. 21.
    M. S. Chambers, N. R. Curtis, A. M. MacLeod, R. J. Maxey, and H. J. Szekeres, US Pat. Appl. 2005101586 (2005).Google Scholar
  22. 22.
    A. Wiersema and S. Gronowitz, Acta Chem. Scand., 24, 2593 (1970).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • N. T. Pokhodylo
    • 1
    Email author
  • O. Ya. Shyyka
    • 1
  • N. D. Obushak
    • 1
  1. 1.Ivan Franko National University of LvivLvivUkraine

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