Skip to main content
SpringerLink
Log in

Polymeric catalyst for the synthesis of new pyrido[2,3-b]indoles

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

Abstract

A new and efficient method has been developed for the one-pot synthesis of novel 2,9-dihydro-2-oxo-4-aryl-1H-pyrido[2,3-b]indole-3-carbonitrile derivatives by condensation of substituted (triethoxymethyl)arene, 1-methyl-1H-indol-2-ol and cyanoacetamide in the presence of a catalytic amount of crosslinked poly(2-acrylamido-2-methyl propane sulfonic acid) (AMPS) as an efficient and heterogeneous catalyst. This polymeric solid acid catalyst is stable and can be easily recovered and reused without significant change in its activity.

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
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. C. Moquin-Pattey, M. Guyot, Tetrahedron 45, 3445 (1989)

    Article  CAS  Google Scholar 

  2. A.A. Semenov, V.V. Tolstikhina, Khim. Geterotsikl. Soedin. 4, 435 (1984)

    Google Scholar 

  3. L. Kaczmarek, P. Nantka-Namirski, Pol. J. Pharmacol. Pharm. 33, 121 (1981)

    Article  CAS  Google Scholar 

  4. N. Helbecque, J.L. Bemier, J.P. Henichard, E. Morel, C. Moquin, M. Guyot, Cancer Biochem. Biophys. 9, 271 (1987)

    CAS  Google Scholar 

  5. A. Khosropour, Can. J. Chem. 86, 264 (2008)

    Article  CAS  Google Scholar 

  6. W. Wang, W. Cheng, L. Shao, J. Yang, Catal. Lett. 121, 77 (2008)

    Article  CAS  Google Scholar 

  7. P. Wasserscheid, M. Sesing, W. Korth, Green Chem. 4, 134 (2002)

    Article  CAS  Google Scholar 

  8. D.Q. Xu, W. Yang, S.P. Luo, B.T. Wang, J. Wu, Z.Y. Xu, Eur. J. Org. Chem. 6, 1007 (2007)

    Article  Google Scholar 

  9. M. Meyer, M. Guyot, Tetrahedron Lett. 37, 4931 (1996)

    Article  CAS  Google Scholar 

  10. P. Molina, P.M. Fresneda, M.A. Sanz, Tetrahedron Lett. 39, 6909 (1997)

    Article  Google Scholar 

  11. S. Achab, M. Guyot, P. Potier, Tetrahedron Lett. 36, 2615 (1995)

    Article  CAS  Google Scholar 

  12. S. Achab, M. Guyot, P. Potier, Tetrahedron Lett. 34, 2127 (1993)

    Article  CAS  Google Scholar 

  13. E.M. Beccalli, F. Clerici, A. Marchesini, Tetrahedron 57, 4787 (2001)

    Article  CAS  Google Scholar 

  14. O. Barun, P.K. Patra, H. Iia, H. Jumjappa, Tetrahedron Lett. 40, 3797 (1999)

    Article  CAS  Google Scholar 

  15. P. Molina, M. Alajarin, A. Vidal, A.P. Sanchez, J. Org. Chem. 57, 929 (1992)

    Article  CAS  Google Scholar 

  16. P. Molina, P.M. Fresneda, Synthesis, 878 (1998)

  17. D.C. Bailey, S.H. Langer, Chem. Rev. 81, 109 (1981)

    Article  CAS  Google Scholar 

  18. N.E. Leadbeater, M. Macro, Chem. Rev. 102, 3217 (2002)

    Article  CAS  Google Scholar 

  19. A. Pourjavadi, H. Salimi, S. Barzegar, B. Eftekhari-Sis, Acta Chim. Slov. 54, 140 (2007)

    CAS  Google Scholar 

  20. S. Damavandi, R. Sandaroos, Heterocycl. Commun. 17, 121 (2011)

    Article  Google Scholar 

  21. S. Damavandi, R. Sandaroos, Monatsh Chem. (2012). doi:10.1007/s00706-012-0744-2

    Google Scholar 

  22. R. Sandaroos, S. Damavandi, M. Salimi, A. Mohammadi, A. Karimian, M. Hasanpour, Mol. Divers. (2012). doi:10.1007/s11030-012-9356-3

    Google Scholar 

  23. S. Damavandi, R. Sandaroos, M. Pashirzad, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0518-9

    Google Scholar 

  24. S. Damavandi, R. Sandaroos, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0681-z

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

    Gholam Hossein Zohuri

  2. Department of Chemistry, Sarvestan Branch, Islamic Azad University, Sarvestan, Iran

    Saman Damavandi

  3. Department of Chemistry, Faculty of Science, Birjand University, Birjand, Iran

    Reza Sandaroos

Authors
  1. Gholam Hossein Zohuri
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Saman Damavandi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Reza Sandaroos
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Gholam Hossein Zohuri or Saman Damavandi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zohuri, G.H., Damavandi, S. & Sandaroos, R. Polymeric catalyst for the synthesis of new pyrido[2,3-b]indoles. Res Chem Intermed 39, 2115–2121 (2013). https://doi.org/10.1007/s11164-012-0743-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0743-2

Keywords

Search

Navigation