Skip to main content
Log in

Solid acid catalyst TS-1 zeolite-assisted solvent-free one-pot synthesis of poly-substituted 2,4,6-triaryl-pyridines

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

Abstract

A new method is described for one-pot solvent-free synthesis of 2,4,6-triaryl pyridines in the presence of a solid acid catalyst, titanium silicate (TS-1) via cyclocondensation of acetophenone, aryl aldehyde and ammonium acetate. The present method illustrates several advantages, such as eco-friendly reaction conditions, simplicity, short reaction time (3 h), easy separation of catalyst and high yields of the products (85–93%). Furthermore, the TS-1 catalyst was reused for four catalytic cycles with consistent catalytic activity.

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
Fig. 1
Scheme 2
Fig. 2

Similar content being viewed by others

References

  1. W. Zhao, F.E. Chen, Cur. Org. Syn. 9, 873 (2012)

    Article  CAS  Google Scholar 

  2. P. Martins, J. Jesus, S. Santos, L.R. Raposo, C.R. Rodrigues, P.V. Baotusta, A.R. Fernandes, Molecules 20, 16852 (2015)

    Article  CAS  Google Scholar 

  3. A. Ahmad, A. Husain, S.A. Khan, M. Mujeeb, A. Bhandari, J. Saudi Chem. Soc. 20, 577 (2016)

    Article  CAS  Google Scholar 

  4. R. Karki, C. Park, K.Y. Jun, J.G. Jee, J.H. Lee, P. Thapa, T.M. Kadayat, Y. Kwon, E.S. Lee, Eur. J. Med. Chem. 84, 555 (2014)

    Article  CAS  Google Scholar 

  5. S. Samshuddin, B. Narayana, D.N. Shettyand, R. Raghavendra, Der Pharma Chemika 3, 232 (2011)

    CAS  Google Scholar 

  6. R. Khajuria, P. Kannaboina, K.K. Kapoor, A. Gupta, G. Raina, A.K. Jassal, L.K. Rana, M.S. Hundal, P. Das, Org. Biomol. Chem. 13, 5944 (2015)

    Article  CAS  Google Scholar 

  7. G. Bist, S. Park, C. Song, T.B.T. Magar, A. Shrestha, Y. Kwon, E.S. Lee, Eur. J. Med. Chem. 133, 69 (2017)

    Article  CAS  Google Scholar 

  8. A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, A. Zare, A.R. Pourali, R. Ayazi-Nasrabadi, Synlett 25, 193 (2014)

    Article  CAS  Google Scholar 

  9. L. Yasmin, P.K. Eggers, B.W. Skelton, K.A. Stubbs, C.L. Raston, Green Chem. 16, 3450 (2014)

    Article  CAS  Google Scholar 

  10. V. Kimesova, M. Sovoboda, K. Waisser, M. Pour, J. Kaustova, IL Farmaco 54, 666 (1999)

    Article  Google Scholar 

  11. I.J. Enyedy, S. Sakamuri, W.A. Zaman, K.M. Johnson, S. Wang, Med. Chem. Lett. 13, 513 (2003)

    Article  CAS  Google Scholar 

  12. A. Winter, C. Friebe, M.D. Hager, U. S. Schubert, Ero. J. Org. Chem. (6), 801 (2009)

  13. M.M. Heravi, K. Bakhtiari, Z. Daroogheha, F.F. Bamoharram, Catal. Commun. 8, 1991 (2007)

    Article  CAS  Google Scholar 

  14. H. Alinezhad, M. Tajbakhsh, N. Ghobadi, Syn. Commun. 45, 1964 (2015)

    Article  CAS  Google Scholar 

  15. M.R.M. Shafiee, R. Moloudi, J. Chem. Res. 35, 294 (2011)

    Article  CAS  Google Scholar 

  16. P.V. Shende, V.B. Labade, J.B. Gujar, B.B. Shingte, M.S. Shingare, Tetrahedron Lett. 53, 1523 (2012)

    Article  Google Scholar 

  17. M.R.M. Shafiee, R. Moloudi, M. Ghashang, APCBEE Procedia 1, 221 (2012)

    Article  Google Scholar 

  18. P. Rajput, N.J.P. Subhashini, Shivaraj, J. Sci. Res. 2, 337 (2010)

    Article  CAS  Google Scholar 

  19. E. Tabrizian, A. Amoozadeh, S. Rahmani, E. Imanifar, S. Azhari, M. Malmir, Chi. Chem. Lett. 26, 1278 (2015)

    Article  CAS  Google Scholar 

  20. M.R.M. Shafiee, R. Moloudi, Lett. Org. Chem. 8, 719 (2011)

    Google Scholar 

  21. R.S. Rohokale, B. Koenig, D.D. Dhavale, J. Org. Chem. 81, 7121 (2016)

    Article  CAS  Google Scholar 

  22. M. Kamli, Cogent Chem. 2, 1171123 (2016)

    Google Scholar 

  23. V. Kannan, K. Sreekumar, Mod. Res. Catal. 2, 42 (2013)

    Article  Google Scholar 

  24. J. Safari, S.G. Ravandi, M.B. Borujeni, J. Chem. Sci. 125, 1063 (2013)

    Article  CAS  Google Scholar 

  25. Z. Zarnegar, J. Safari, M.B. Borujeni, Chem. Hete. Comp. 501, 683 (2015)

    Google Scholar 

  26. Z.L. Min, T.Z. Yin, X.M. Hu, Asian J. Chem. 26, 7977 (2014)

    Article  Google Scholar 

  27. S. Mahernia, M. Adib, M. Mahdavi, M. Nosrati, Tetrahedron Lett. 55, 3844 (2014)

    Article  CAS  Google Scholar 

  28. A. Thangaraj, M.J. Eapen, S. Sivasanker, P. Ratnasamy, Zeolites 12, 943 (1992)

    Article  CAS  Google Scholar 

  29. M. Taramasso, U. S. Patent 4, 410 (1983)

    Google Scholar 

  30. H.F. Youssef, W.H. Hegazy, H.H. Abo-almaged, G.T. El-Bassyouni, Bioinorg. Chem. App. 12, 428121 (2015)

    Google Scholar 

  31. M. Opanasenko, A. Dhakshinamoorthy, M. Shamzhy, P. Nachtigall, M. Horacek, H. Garcia, J. Cejka, J. Catal. Sci. Technol. 3, 500 (2013)

    Article  CAS  Google Scholar 

  32. N. Wilde, M. Pelz, S.G. Gebhardt, R. Glaser, Green Chem. 17, 3378 (2015)

    Article  CAS  Google Scholar 

  33. M.G. Clerici, O.A. Kholdeeva, Liquid Phase Oxidation Via Heterogeneous Catalysis, Firsted (Wiley, Hoboken, 2013)

    Book  Google Scholar 

  34. Y. Hayashi, Chem. Sci 7, 866 (2016)

    Article  CAS  Google Scholar 

  35. C. Abraham, G.M. Dmitry, K. Steven, B. Timothy, D.B. Jonathan Milton, J. Solvent Extr. Ion Exch. 30, 229 (2012)

    Article  Google Scholar 

  36. K. Moller, T. Bein, Chem. Soc. Rev. 42, 3689 (2013)

    Article  Google Scholar 

  37. C.K. Banerjee, J.D. Umarye, P.R. Kanjilal, Synth. Commun. 43, 2208 (2013)

    Article  CAS  Google Scholar 

  38. E.G. Derouane, J.C. Vedrine, R.R. Pinto, M.P. Borges, L. Costa, M.A.N.D.A. Lemos, F. Lemos, F.R. Ribeiro, Catal. Rev. Sci. Eng. 55, 454 (2013)

    Article  CAS  Google Scholar 

  39. J. Zhuaung, Z. Yan, X. Liu, X. Liu, X. Han, X. Bao, U. Mueller, Catal. Lett. 83, 1 (2002)

    Article  Google Scholar 

  40. S. P. Gadekar, G. T. Pawar, R. R. Magar, M. K. Lande, Polycycl. Aromat. Compd. (2017)

  41. G.T. Pawar, S.P. Gadekar, B.R. Arbad, M.K. Lande, Bull. Chem. Rea. Eng. Catal. 12, 32 (2016)

    Article  Google Scholar 

  42. M.M. Treacy, J.B. Higgins, Collection of Simulated XRD Powder Patterns for Zeolites (Elsevier, Amsterdam, 2001), p. 236

    Book  Google Scholar 

  43. Y. Xue, Y. Xie, H. Wei, Y. Wen, X. Wang, B. Li, New J. Chem. 38, 4229 (2014)

    Article  CAS  Google Scholar 

  44. X. Wang, Y. Guo, X. Zhang, Y. Wang, H. Liu, J. Wang, J. Qiua, K.L. Yeung, Chem. Eng. J. 156, 562 (2010)

    Article  CAS  Google Scholar 

  45. R. Barakov, N. Shcherban, P. Yaremov, V. Solomakha, A. Yshnevskyy, V. Ilyin, J. Porous Mat. 23, 517 (2016)

    Article  CAS  Google Scholar 

  46. A.B. Gambhire, M.K. Lande, S.B. Rathod, B.R. Arbad, K.N. Vidhate, R.S. Gholap, K.R. Patil, Arab. J. Chem. 6, s429 (2016)

    Article  Google Scholar 

  47. G. Ricchiardi, A. Damin, S. Bordiga, C. Lamberti, G. Spano, F. Rivetti, A. Zecchinna, J. Am. Chem. Soc. 123, 11409 (2001)

    Article  CAS  Google Scholar 

  48. A.C.K. Yip, F.L.Y. Lam, X. Hu, P. Li, W.K. Yuan, Ind. Eng. Chem. Res. 48, 5266 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad–431004 (MS), India, for his support and constant encouragement during the progress of this work and for providing necessarily laboratory facilities. The corresponding author, MKL, is grateful to UGC New Delhi for providing financial support under major research project F. No. 43-184/2014 (SR). The authors are grateful to STIC Cochin and SAIF Chandigarh for characterization facilities.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Machhindra K. Lande.

Electronic supplementary material

Below is the link to the electronic supplementary material.

11164_2018_3305_MOESM1_ESM.docx

Full experimental details and 1H, 13C NMR, HRMS spectra, XRD. BET, SEM FTIR, of other products in the “supplementary content” of this article web page are available. (DOCX 1110 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gadekar, S.P., Lande, M.K. Solid acid catalyst TS-1 zeolite-assisted solvent-free one-pot synthesis of poly-substituted 2,4,6-triaryl-pyridines. Res Chem Intermed 44, 3267–3278 (2018). https://doi.org/10.1007/s11164-018-3305-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3305-4

Keywords

Navigation