Advertisement

Chemistry of Heterocyclic Compounds

, Volume 55, Issue 4–5, pp 435–441 | Cite as

Synthesis of thieno[2,3-b]pyrrole-2(4)-carboxylic and 2,4-dicarboxylic acids

  • Alina N. GrozavEmail author
  • Mariana Z. Fedoriv
  • Vitaliy A. Chornous
  • Alina A. Palamar
  • Mykhailo K. Bratenko
  • Mykhailo V. Vovk
Article
  • 13 Downloads

1-Substituted 5-chloro-4-formylpyrrole-3-carboxylates reacted with thioglycolic acid or ethyl thioglycolate in EtOH containing EtONa at room temperature, forming 4-(ethoxycarbonyl)thieno[2,3-b]pyrrole-2-carboxylic acids or thieno[2,3-b]pyrrole-2,4-dicarboxylates. Cyclocondensation with thioglycolic acid upon refluxing in K2CO3–DMF system was accompanied by decarboxylation and led to the formation of thieno[2,3-b]pyrrole-4-carboxylates. Hydrolysis of the obtained carboxylates with LiOH provided thieno[2,3-b]pyrrole-2(4)-carboxylic and 2,4-dicarboxylic acids.

Keywords

5-chloro-4-formylpyrrole-3-carboxylates ethyl thioglycolate thieno[2,3-b]pyrrolecarboxylates thieno[2,3-b]pyrrolecarboxylic acids thioglycolic acid alkaline hydrolysis cyclocondensation 

References

  1. 1.
    Whittamore, P. R. O.; Addie, M. S.; Bennett, S. N. L.; Birch, A. M.; Butters, M.; Godfrey, L.; Kenny, P. W.; Morley, A. D.; Murray, P. M.; Oikonomakos, N. G.; Otterbein, L. R.; Pannifer, A. D.; Parker, J. S.; Readman, K.; Siedlecki, P. S.; Schofield, P.; Stocker, A.; Taylor, M. J.; Townsend, L. A.; Whalley, D. P.; Whitehouse, J. Bioorg. Med. Chem. Lett. 2006, 16, 5567.CrossRefGoogle Scholar
  2. 2.
    Birch, A. M.; Kenny, P. W.; Oikonomakos, N. G.; Otterbein, L.; Schofield, P.; Whittamore, P. R. O.; Whalley, D. P. Bioorg. Med. Chem. Lett. 2007, 17, 394.CrossRefGoogle Scholar
  3. 3.
    Birch, A. M.; Johnstone, G.; Plowright, A. T.; Simpson, I. WO Patent 2006082401A1.Google Scholar
  4. 4.
    Bennett, S. N. L.; Simpson, I. WO Patent 2005020986A1.Google Scholar
  5. 5.
    Birch, A. M.; Morley, A. D.; Stocker, A.; Whittamore, P. R. Q. WO Patent 2003074532A1.Google Scholar
  6. 6.
    Bartlett, J. B.; Freeman, S.; Kenny, P.; Morley, A.; Whittamore, P. US Patent 20030232875A1.Google Scholar
  7. 7.
    Sartori, L.; Mercurio, C.; Amigoni, F.; Cappa, A.; Fagá, G.; Fottori, R.; Legnaghi, E.; Ciossani, G.; Mattevi, A.; Meroni, G.; Moretti, L.; Cecatiello, V.; Pasqualato, S.; Romussi, A.; Thaler, F.; Trifiró, P.; Villa, M.; Vultaggio, S.; Botrugno, O. A.; Dessanti, P.; Minucci, S.; Zagarrí, E.; Carettoni, D.; Iuzzolino, L.; Varasi, M.; Vianello, P. J. Med. Chem. 2017, 60, 1673.CrossRefGoogle Scholar
  8. 8.
    Sparey, T.; Abeywickrema, P.; Almond, S.; Brandon, N.; Byrne, N.; Campbell, A.; Hutson, P. H.; Jacobson, M.; Jones, B.; Munshi, S.; Pascarella, D.; Pike, A.; Prasad, G. S.; Sachs, N.; Sakatis, M.; Sardana, V.; Venkatraman, S.; Young, M. B. Bioorg. Med. Chem. Lett. 2008, 18, 3386.CrossRefGoogle Scholar
  9. 9.
    Ching, K.-C.; Tran, T. N. Q.; Amrun, S. N.; Kam, Y.-W.; Ng, L. F. P.; Chai, C. L. L. J. Med. Chem. 2017, 60, 3165.CrossRefGoogle Scholar
  10. 10.
    Venable, J. D.; Cai, H.; Chai, W.; Dvorak, C. A.; Grice, C. A.; Jablonowski, J. A.; Shah, C. R.; Kwok, A. K.; Ly, K. S.; Pio, B.; Wei, J.; Desai, P. J.; Jiang, W.; Nguyen, S.; Ling, P.; Wilson, S. J.; Dunford, P. J.; Thurmond, R. L.; Lovenberg, T. W.; Karlsson, L.; Carruthers, N. I.; Edwards, J. P. J. Med. Chem. 2005, 48, 8289.CrossRefGoogle Scholar
  11. 11.
    Arnould, J.-C.; Harris, C. S.; Jones, P. WO Patent 2005080402A1.Google Scholar
  12. 12.
    Sommen, G.; Comel, A.; Kirsch, G. Synlett 2001, 1731.Google Scholar
  13. 13.
    Cai, Q.; Li, Z.; Wei, J.; Ha, C.; Pei, D.; Ding, K. Chem. Commun. 2009, 7581.Google Scholar
  14. 14.
    Sommen, G.; Comel, A.; Kirsch, G. Tetrahedron 2003, 59, 1557.CrossRefGoogle Scholar
  15. 15.
    Wei, H.; Cai, J.; Sun, M.; Ji, M. Heteroat. Chem. 2007, 18, 236.CrossRefGoogle Scholar
  16. 16.
    Malancona, S.; Hernando, J. I. M.; Attenni, B.; Ontoria, J. M.; Narjes, F. Tetrahedron Lett. 2009, 50, 1625.CrossRefGoogle Scholar
  17. 17.
    Bonafoux, D.; Abibi, A.; Bettencourt, B.; Burchat, A.; Ericsson, A.; Harris, C. M.; Kebede, T.; Morytko, M.; McPherson, M.; Wallace, G.; Wu, X. Bioorg. Med. Chem. Lett. 2011, 21, 1861.CrossRefGoogle Scholar
  18. 18.
    Metten, B.; Kostermans, M.; Van Baelen, G.; Smet, M.; Dehaen, W. Tetrahedron 2006, 62, 6018.CrossRefGoogle Scholar
  19. 19.
    Barman, G.; Ray, J. K. J. Heterocycl. Chem. 2011, 48, 218.CrossRefGoogle Scholar
  20. 20.
    Olsen, R. K.; Snyder, H. R. J. Org. Chem. 1965, 30, 184.CrossRefGoogle Scholar
  21. 21.
    Lovren, F.; Gaon, I. D.; Bobarevic, B. Pharmazie 1992, 47, 773.Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Alina N. Grozav
    • 1
    Email author
  • Mariana Z. Fedoriv
    • 2
  • Vitaliy A. Chornous
    • 1
  • Alina A. Palamar
    • 1
  • Mykhailo K. Bratenko
    • 1
  • Mykhailo V. Vovk
    • 3
  1. 1.Bukovinian State Medical UniversityChernivtsiUkraine
  2. 2.Ivano-Frankivsk National Medical UniversityIvano-FrankivskUkraine
  3. 3.Institute of Organic ChemistryNational Academy of Sciences of UkraineKyivUkraine

Personalised recommendations