Skip to main content
SpringerLink
Log in

Catalyst-free rapid synthesis of benzo[4,5]imidazo[1,2-a]-pyrimidine-3-carboxamides via four-component coupling in one pot

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A new class of fused tricyclic benzo[4,5]imidazo[1,2-a]-pyrimidine-3-carboxamide derivatives was synthesized via an environmentally benign one pot sequential four-component condensation reaction of an amine, 2,2,6-trimethyl-4H-1,3-dioxin-4-one, an aldehyde and 1H-benzo[d]imidazol-2-amine without using catalyst in good yields.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. C.O. Kappe, Eur. J. Med. Chem. 35, 1043 (2000)

    Article  CAS  Google Scholar 

  2. C.O. Kappe, W.M.F. Fabian, Tetrahedron 53, 2803 (1997)

    Article  CAS  Google Scholar 

  3. C.O. Kappe, Tetrahedron 49, 6937 (1993)

    Article  CAS  Google Scholar 

  4. B.B. Snider, Z. Shi, J. Org. Chem. 58, 3828 (1993)

    Article  CAS  Google Scholar 

  5. L.E. Overman, M.H. Rabinowitz, P.A. Renhowe, J. Am. Chem. Soc. 117, 2657 (1995)

    Article  CAS  Google Scholar 

  6. K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S.A. Moreland, B.C. O’Reilly, J. Med. Chem. 34, 806 (1991)

    Article  CAS  Google Scholar 

  7. K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smilie, M.F. Mallay, J. Med. Chem. 33, 2629 (1990)

    Article  CAS  Google Scholar 

  8. J. Kempson, W.J. Pitts, J. Barbosa, J. Guo, O. Omotoso, A. Watson, K. Stebbins, G.C. Starling, J.H. Dodd, J.C. Barrish, R. Felix, K. Fischer, Bioorg. Med. Chem. Lett. 15, 1829 (2005)

    Article  CAS  Google Scholar 

  9. N. Zanatta, S.S. Amaral, A. Esteves-Souza, A. Echevarria, P.B. Brondani, D.C. Flores, H.G. Bonacorso, A.F.C. Flores, M.A.P. Martins, Synthesis 2305 (2006)

  10. J.J. Nunes, X.T. Zhu, M. Ermann, C. Ghiron, D.N. Johnston, C.-G.P. Saluste, WO 2005021551, 2005 [Chem. Abstr. 2005, 142, 298123]

  11. A.A.M. Abdel-Hafez, Arch. Pharm. Res. 30, 678 (2007)

    Article  CAS  Google Scholar 

  12. V.V. Lipson, V.D. Orlov, S.M. Desenko, S.V. Shishkina, O.V. Shishkin, M.G. Shirobokova, Chem. Heterocycl. Compd. 36, 1039 (2001)

    Article  Google Scholar 

  13. S.L. Schreiber, Science 287, 1964 (2000)

    Article  CAS  Google Scholar 

  14. D.R. Spring, Org. Biomol. Chem. 1, 3867 (2003)

    Article  CAS  Google Scholar 

  15. M.D. Burke, E.M. Berger, S.L. Schreiber, Science 302, 5645 (2003)

    Article  Google Scholar 

  16. M.D. Burke, S.L. Schreiber, Angew. Chem. Int. Ed. 43, 46 (2004)

    Article  Google Scholar 

  17. D.S. Tan, Nat. Chem. Biol. 1, 74 (2005)

    Article  CAS  Google Scholar 

  18. L.A. Wessjohann, E. Ruijter, Top. Curr. Chem. 243, 137 (2005)

    CAS  Google Scholar 

  19. R.J. Spandl, A. Bender, D.R. Spring, Org. Biomol. Chem. 6, 1149 (2008)

    Article  CAS  Google Scholar 

  20. M.N. Ivantsova, M.I. Tokareva, M.A. Mironov, Chem. Heterocycl. Compd. 48, 584 (2012)

    Google Scholar 

  21. R.P. Gore, A.P. Rajput, Drug Invention Today 5, 148 (2013)

    Google Scholar 

  22. D.J. Ramón, M. Yus, Angew. Chem. Int. Ed. 44, 1602 (2005)

    Article  Google Scholar 

  23. A. Dömling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  24. F. Liéby-Muller, C. Simon, T. Constantieux, J. Rodriguez, QSAR Comb. Sci. 25, 432 (2006)

    Article  Google Scholar 

  25. G. Guillena, D.J. Ramón, M. Yus, Tetrahedron: Asymmetry 18, 693 (2007)

    CAS  Google Scholar 

  26. N. Isambert, R. Lavilla, Chem. Eur. J. 14, 8444 (2008)

    Article  CAS  Google Scholar 

  27. T.H. Istvan, T.A. Paul, Chem. Rev. 107, 2167 (2007)

    Article  Google Scholar 

  28. I.T. Horvath, Chem. Rev. 35, 685 (2002)

    CAS  Google Scholar 

  29. J.N. Tan, H. Li, Y. Gu, Green Chem. 12, 1772 (2010)

    Article  CAS  Google Scholar 

  30. D. Bradley, G. Williams, A. Cullen, A. Fourie, H. Henning, M. Lawton, W. Mommsen, P. Nangu, J. Parker, A. Renison, Green Chem. 12, 1919 (2010)

    Article  Google Scholar 

  31. A. Solhy, A. Elmakssoudi, R. Tahir, M. Karkouri, M. Larzek, M. Bousmina, M. Zahouily, Green Chem. 12, 2261 (2010)

    Article  CAS  Google Scholar 

  32. G. Choudhary, R.K. Peddinti, Green Chem. 13, 276 (2011)

    Article  CAS  Google Scholar 

  33. S. Kumar, P. Sharma, K.K. Kapoor, M.S. Hundal, Tetrahedron 64, 536 (2008)

    Article  CAS  Google Scholar 

  34. J. Zhang, Z. Cui, F. Wang, Y. Wang, Z. Miao, R. Chen, Green Chem. 9, 1341 (2007)

    Article  CAS  Google Scholar 

  35. A. Shaabani, M. Seyyedhamzeh, A. Maleki, F. Rezazadeh, M. Behnam, J. Comb. Chem. 11, 375 (2009)

    Article  CAS  Google Scholar 

  36. A. Shaabani, M. Seyyedhamzeh, A. Maleki, M. Behnam, F. Rezazadeh, Tetrahedron Lett. 50, 2911 (2009)

    Article  CAS  Google Scholar 

  37. A. Shaabani, M. Seyyedhamzeh, A. Maleki, M. Behnam, Tetrahedron Lett. 50, 6355 (2009)

    Article  CAS  Google Scholar 

  38. A. Shaabani, M. Seyyedhamzeh, A. Maleki, F. Hajishaabanha, Tetrahedron 66, 4040 (2010)

    Article  CAS  Google Scholar 

  39. A. Shaabani, A. Maleki, F. Hajishaabanha, H. Mofakham, M. Seyyedhamzeh, M. Mahyari, S.W. Ng, J. Comb. Chem. 12, 186 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge financial support from the Iran National Elites Foundation (INEF), Research Council of Shahid Beheshti University and Ministry of Higher Education of Malaysia (Grant No. UM.C/HIR/MOHE/SC/12).

Author information

Authors and Affiliations

  1. Department of Chemistry, Shahid Beheshti University, G. C., P.O. Box 19396-4716, Tehran, Iran

    Ahmad Shaabani, Mozhdeh Seyyedhamzeh & Nasim Ganji

  2. Department of Chemistry, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Seik Weng Ng

Authors
  1. Ahmad Shaabani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mozhdeh Seyyedhamzeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nasim Ganji
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Seik Weng Ng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ahmad Shaabani.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material (DOC 11140 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shaabani, A., Seyyedhamzeh, M., Ganji, N. et al. Catalyst-free rapid synthesis of benzo[4,5]imidazo[1,2-a]-pyrimidine-3-carboxamides via four-component coupling in one pot. J IRAN CHEM SOC 11, 481–487 (2014). https://doi.org/10.1007/s13738-013-0321-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-013-0321-6

Keywords

Search

Navigation