Skip to main content
SpringerLink
Log in

An effective lactic acid-modified Hβ zeolite for synthesis of bis(indolyl)methanes

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

Abstract

Excellent activity and stability have been observed for a lactic acid-modified Hβ (LA-Hβ) zeolite in the synthesis of bis(indolyl)methanes by Friedel–Crafts alkylation of indole with aldehydes. It is proposed that lactic acid treatment is appropriate for dealumination of Hβ zeolite, and results in a LA-Hβ zeolite with greater surface area, fewer weak acid sites, and more moderately-strong acid sites, as confirmed by the Brunauer–Emmett–Teller method, inductively coupled plasma emission spectrometry, and temperature-programmed desorption of NH3. Moreover, both electronic and steric effects of substituents on the aromatic ring of the aldehydes were found to be important in this reaction.

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

Similar content being viewed by others

References

  1. Y.F. Du, R.H. Liu, G. Linn, K. Zhao, Org. Lett. 8, 5919 (2006)

    Article  CAS  Google Scholar 

  2. H.J. Wadsworth, B. Shan, D. O’shea, J.M. Passsmore, W.J. Trigg, A. Ewan, US Patent 0020884 (2012)

  3. G. Giannini, M. Marzi, M.D. Marzo, G. Battistuzzi, R. Pezzi, T. Bruneti, W. Cabri, L. Vesci, C. Pisano, Bioorg. Med. Chem. Lett. 19, 2840 (2009)

    Article  CAS  Google Scholar 

  4. S. Safe, S. Papineni, S. Chintharlapalli, Cancer Lett. 269, 326 (2008)

    Article  CAS  Google Scholar 

  5. M. York, M. Abdelrahim, S. Chintharlapalli, S.D. Lucero, S. Safe, Clin. Cancer Res. 13, 6743 (2007)

    Article  CAS  Google Scholar 

  6. G. Babu, N. Sridhar, P.T. Perumal, Synth. Commun. 30, 3609 (2000)

    Article  Google Scholar 

  7. B.V. Gregorvich, K.S.Y. Liang, D.M. Clugston, S.F. Macdonald, Can. J. Chem. 46, 3291 (1968)

    Article  Google Scholar 

  8. M.W. Roomi, S.F. Macdonald, Can. J. Chem. 48, 139 (1970)

    Article  CAS  Google Scholar 

  9. C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 345, 557 (2003)

    Article  CAS  Google Scholar 

  10. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A Chem. 253, 249 (2006)

    Article  CAS  Google Scholar 

  11. H. Firouzabadi, N. Iranpoor, A.A. Jafari, J. Mol. Catal. A Chem. 244, 168 (2006)

    Article  CAS  Google Scholar 

  12. K. Bachari, R. Chebout, R.M. Guerroudj, M. Lamouchi, Res. Chem. Intermed. 38, 367 (2012)

    Article  CAS  Google Scholar 

  13. P.P. Pescarmona, B.C. Gagea, P. Van der Aa, P.A. Jacobs, J.A. Martens, Catal. Today 159, 120 (2011)

    Article  CAS  Google Scholar 

  14. A.V. Reddy, K. Ravinder, V.L.N. Reddy, T.V. Goud, V.Y. Ravikanth, Y. Venkateswarlu, Synth. Commun. 33, 3687 (2003)

    Article  Google Scholar 

  15. M. Karthik, A.K. Tripathi, N.M. Gupta, M. Palanichamy, V. Murugesan, Catal. Commun. 5, 371 (2004)

    Article  CAS  Google Scholar 

  16. M. Karthik, C.J. Magesh, P.T. Perumal, M. Palanichamy, B. Arabindoo, V. Murugesan, Appl. Catal. A Gen. 286, 137 (2005)

    Article  CAS  Google Scholar 

  17. Y. Fan, X.J. Bao, X.Y. Lin, G. Shi, H.Y. Liu, J. Phys. Chem. B 110, 15411 (2006)

    Article  CAS  Google Scholar 

  18. M.R. Apelian, A.S. Fung, G.J. Kennedy, T.F. Degnan, J. Phys. Chem. 100, 16577 (1996)

    Article  CAS  Google Scholar 

  19. G.Y. Bai, Y.H. Yang, Z. Ma, J.Z. Xu, M.D. Qiu, F. He, X.L. Yan, H.Y. Dou, Res. Chem. Intermed. 38, 795 (2012)

    Article  CAS  Google Scholar 

  20. R. Srivastava, N. Iwasa, S.I. Fujita, M. Arai, Catal. Lett. 130, 655 (2009)

    Article  CAS  Google Scholar 

  21. G.Y. Bai, K. Xu, G.F. Chen, Y.H. Yang, T.Y. Li, Synthesis 10, 1599 (2011)

    Article  Google Scholar 

  22. Z.K. Xie, Q.L. Chen, C.F. Zhang, J.Q. Bao, Y.H. Cao, J. Phys. Chem. B 104, 2853 (2000)

    Article  CAS  Google Scholar 

  23. D.F. Jin, B. Zhu, Z.Y. Hou, J.H. Fei, H. Lou, X.M. Zheng, Fuel 86, 2707 (2007)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support by the National Natural Science Foundation of China (20806018), the Natural Science Foundation of Hebei Province (B2011201017), and the Science Project of the Hebei Education Department (ZD200910) are gratefully acknowledged.

Author information

Authors and Affiliations

  1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, No.180 Wusi East Road, Baoding, 071002, Hebei, People’s Republic of China

    Guo Yi Bai, Zheng Ma, Lingjuan Shi, Tianyu Li, Jie Han, Guofeng Chen, Na Li & Peide Liu

Authors
  1. Guo Yi Bai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zheng Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lingjuan Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tianyu Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jie Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Guofeng Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Na Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Peide Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Guo Yi Bai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bai, G.Y., Ma, Z., Shi, L. et al. An effective lactic acid-modified Hβ zeolite for synthesis of bis(indolyl)methanes. Res Chem Intermed 38, 2501–2510 (2012). https://doi.org/10.1007/s11164-012-0567-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0567-0

Keywords

Search

Navigation