Skip to main content
Log in

Copper(I)-catalyzed synthesis of thienopyrazoloquinazolinone derivatives under ligand-free conditions

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A series of fused tetracyclic thieno[3′,2′:3,4]pyrazolo[5,1-b]quinazolin-6(4H)-one derivatives were synthesized by reaction of 2-aminobenzohydrazide and 3-bromothiophene-2-carbaldehyde in good yields. The reaction includes subsequent condensation, cyclization, and CuBr-catalyzed Ullmann-type reaction under ligand-free conditions.

Graphical Abstract

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.

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. R. Gali, J. Banothu, M. Porika, R. Velpula, S. Hnamte, R. Bavantula, S. Abbagani, S. Busi, Bioorg. Med. Chem. Lett. 24, 4239 (2014)

    Article  CAS  Google Scholar 

  2. H. Luo, S.J. Yang, Y.Q. Cai, Z.J. Peng, T. Liu, Eur. J. Med. Chem. 84, 746 (2014)

    Article  CAS  Google Scholar 

  3. S. Nahar, D. Bose, P.S. Kumar, S. Saha, S. Maiti, Chem. Commun. 50, 4639 (2014)

    Article  CAS  Google Scholar 

  4. N. Raghav, M. Singh, Eur. J. Pharm. Sci. 54, 28 (2014)

    Article  CAS  Google Scholar 

  5. R. Sordella, D.W. Bell, D.A. Haber, J. Settleman, Science 305, 1163 (2004)

    Article  CAS  Google Scholar 

  6. A. Nazeer, N. Perveen, M.A. Khan, M.N. Khan, M.A. Munawar, W.-O. Lin, Asian J. Chem. 25, 7705 (2013)

    Article  CAS  Google Scholar 

  7. F. Varano, D. Catarzi, V. Colotta, F.R. Calabri, O. Lenzi, G. Filacchioni, A. Galli, C. Costagli, F. Deflorian, S. Moro, Bioorg. Med. Chem. 13, 5536 (2005)

    Article  CAS  Google Scholar 

  8. R.R. Vidule, S.G. Shirodkar, J. Chem. Pharm. Res. 5, 167 (2013)

    CAS  Google Scholar 

  9. M.A. Hussein, Med. Chem. Res. 22, 4641 (2013)

    Article  CAS  Google Scholar 

  10. C.A. Free, L.E. Hall, J. Pharm. Exp. Ther. 213, 437 (1980)

    CAS  Google Scholar 

  11. S. Taliani, I. Pugliesi, E. Barresi, S. Salerno, C. Marchand, K. Agama, F. Simorini, C. La Motta, A.M. Marini, F.S. Di Leva, L. Marinelli, S. Cosconati, E. Novellino, Y. Pommier, R. Di Santo, F. Da Settimo, J. Med. Chem. 56, 7458 (2013)

    Article  CAS  Google Scholar 

  12. M. Caldarelli, M. Angiolini, T. Disingrini, D. Donati, M. Guanci, S. Nuvoloni, H. Posteri, F. Quartieri, M. Silvagni, R. Colombo, Bioorg. Med. Chem. Lett. 21, 4507 (2011)

    Article  CAS  Google Scholar 

  13. B. Asproni, G. Murineddu, A. Pau, G.A. Pinna, M. Langgard, C.T. Christoffersen, J. Nielsen, J. Kehler, Bioorg. Med. Chem. 19, 642 (2011)

    Article  CAS  Google Scholar 

  14. M. Angiolini, P. Banfi, E. Casale, F. Casuscelli, C. Fiorelli, M.B. Saccardo, M. Silvagni, F. Zuccotto, Bioorg. Med. Chem. Lett. 20, 4095 (2010)

    Article  CAS  Google Scholar 

  15. G.W. Rewcastle, B.D. Palmer, A.J. Bridges, H.D.H. Showalter, L. Sun, J. Nelson, A. McMichael, A.J. Kraker, D.W. Fry, W.A. Denny, J. Med. Chem. 39, 918 (1996)

    Article  Google Scholar 

  16. O. Prien, K. Eis, W. Schwede, J. Guenther, D. Zopf, D. E. A. Brittain, PCT Int. Appl. WO 2007147577 A1 20071227 (2007)

  17. A.M. Al-Obaid, S.G. Abdel-Hamide, H.A. El-Kashef, A.A.-M. Abdel-Aziz, A.S. El-Azab, H.A. Al-Khamees, H.I. El-Subbagh, Eur. J. Med. Chem. 44, 2379 (2009)

    Article  CAS  Google Scholar 

  18. D.S. Chen, G.L. Dou, Y.L. Li, Y. Liu, X.S. Wang, J. Org. Chem. 78, 5700 (2013)

    Article  CAS  Google Scholar 

  19. D.S. Chen, M.M. Zhang, Y.L. Li, Y. Liu, X.S. Wang, Tetrahedron 70, 2889 (2014)

    Article  CAS  Google Scholar 

  20. C. Li, W.T. Zhang, X.S. Wang, J. Org. Chem. 79, 5847 (2014)

    Article  CAS  Google Scholar 

  21. W.T. Zhang, D.S. Chen, L. Chao, X.S. Wang, Synthesis 47, 562 (2015)

    CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the National Natural Science Foundation of China (20802061), the Major Natural Science Foundation of Jiangsu Province (14KJA150004), and a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xiang-Shan Wang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, WT., Chen, DS., Zhang, MM. et al. Copper(I)-catalyzed synthesis of thienopyrazoloquinazolinone derivatives under ligand-free conditions. Res Chem Intermed 42, 6769–6776 (2016). https://doi.org/10.1007/s11164-016-2497-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2497-8

Keywords

Navigation