Skip to main content
Log in

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

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Y. Huang and A. Doemling, Mol. Diversity, 15, 3 (2011).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  3. N. I. Sweidan, M. Z. Nazer, M. M. El-Abadelah, and W. Voelter, Lett. Org. Chem., 7, 79 (2010).

    Article  CAS  Google Scholar 

  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.

  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).

    Article  CAS  Google Scholar 

  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).

    Article  Google Scholar 

  7. J. Sircar, K. C. Sunil Kumar, T. J. Davis, and W. Ying, US Pat. Appl. 7365200.

  8. K. Gewald, E. Schinke, and H. Bottcher, Chem. Ber., 99, 94 (1966).

    Article  CAS  Google Scholar 

  9. V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, Chem. Heterocycl. Compd., 3, 789 (1967). [Khim. Geterotsikl. Soedin., 1010 (1967).]

    Article  Google Scholar 

  10. J. Sice, J. Org. Chem., 19, 70 (1954).

    Article  CAS  Google Scholar 

  11. F. Bohlmann and E. Bresinsky, Chem. Ber., 97, 2109 (1964).

    Article  CAS  Google Scholar 

  12. T. L. Fevig, W. G. Phillips, and P. H. Lau, J. Org. Chem., 66, 2493 (2001).

    Article  CAS  Google Scholar 

  13. T. L. Fevig, P. H. Lau, and W. G. Phillips, EP Pat. Appl. 1023283.

  14. N. Charrier, Z. Liu, and S. Z. Zard, Org. Lett., 14, 2018 (2012).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  16. A. T. Mavrova, D. Wesselinova, Y. A. Tsenov, and P. Denkova, Eur. J. Med. Chem., 44, 63 (2009).

    Article  CAS  Google Scholar 

  17. T. Kohara, H. Tanaka, K. Kimura, H. Horiuchi, K. Seio, M. Arita, T. Fujimoto, and I. Yamamoto, J. Heterocycl. Chem., 39, 163 (2002).

    Article  CAS  Google Scholar 

  18. D. Melandri, P. C. Montevecchi, and M. L. Navacchia, Tetrahedron, 55, 12227 (1999).

    Article  CAS  Google Scholar 

  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).

    Article  Google Scholar 

  20. A. Schöning and W. Friedrichsen, Liebigs Ann. Chem., 405 (1989).

  21. M. S. Chambers, N. R. Curtis, A. M. MacLeod, R. J. Maxey, and H. J. Szekeres, US Pat. Appl. 2005101586 (2005).

  22. A. Wiersema and S. Gronowitz, Acta Chem. Scand., 24, 2593 (1970).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. T. Pokhodylo.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1900-1907, December, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pokhodylo, N.T., Shyyka, O.Y. & Obushak, N.D. Ethyl 2-Aminothiophene-3-Carboxylates in the Synthesis of Isomeric Thienopyridines. Chem Heterocycl Comp 50, 1748–1755 (2015). https://doi.org/10.1007/s10593-015-1647-z

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1647-z

Keywords

Navigation