Advertisement

Research on Chemical Intermediates

, Volume 44, Issue 5, pp 3267–3278 | Cite as

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

  • Sachin P. Gadekar
  • Machhindra K. Lande
Article
  • 133 Downloads

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

Keywords

Titanium silicate (TS-1) One-pot reaction Solid acid catalyst 2,4,6-Triaryl pyridine 

Notes

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.

Supplementary material

11164_2018_3305_MOESM1_ESM.docx (1.1 mb)
Full experimental details and 1 H, 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)

References

  1. 1.
    W. Zhao, F.E. Chen, Cur. Org. Syn. 9, 873 (2012)CrossRefGoogle Scholar
  2. 2.
    P. Martins, J. Jesus, S. Santos, L.R. Raposo, C.R. Rodrigues, P.V. Baotusta, A.R. Fernandes, Molecules 20, 16852 (2015)CrossRefGoogle Scholar
  3. 3.
    A. Ahmad, A. Husain, S.A. Khan, M. Mujeeb, A. Bhandari, J. Saudi Chem. Soc. 20, 577 (2016)CrossRefGoogle Scholar
  4. 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)CrossRefGoogle Scholar
  5. 5.
    S. Samshuddin, B. Narayana, D.N. Shettyand, R. Raghavendra, Der Pharma Chemika 3, 232 (2011)Google Scholar
  6. 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)CrossRefGoogle Scholar
  7. 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)CrossRefGoogle Scholar
  8. 8.
    A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, A. Zare, A.R. Pourali, R. Ayazi-Nasrabadi, Synlett 25, 193 (2014)CrossRefGoogle Scholar
  9. 9.
    L. Yasmin, P.K. Eggers, B.W. Skelton, K.A. Stubbs, C.L. Raston, Green Chem. 16, 3450 (2014)CrossRefGoogle Scholar
  10. 10.
    V. Kimesova, M. Sovoboda, K. Waisser, M. Pour, J. Kaustova, IL Farmaco 54, 666 (1999)CrossRefGoogle Scholar
  11. 11.
    I.J. Enyedy, S. Sakamuri, W.A. Zaman, K.M. Johnson, S. Wang, Med. Chem. Lett. 13, 513 (2003)CrossRefGoogle Scholar
  12. 12.
    A. Winter, C. Friebe, M.D. Hager, U. S. Schubert, Ero. J. Org. Chem. (6), 801 (2009)Google Scholar
  13. 13.
    M.M. Heravi, K. Bakhtiari, Z. Daroogheha, F.F. Bamoharram, Catal. Commun. 8, 1991 (2007)CrossRefGoogle Scholar
  14. 14.
    H. Alinezhad, M. Tajbakhsh, N. Ghobadi, Syn. Commun. 45, 1964 (2015)CrossRefGoogle Scholar
  15. 15.
    M.R.M. Shafiee, R. Moloudi, J. Chem. Res. 35, 294 (2011)CrossRefGoogle Scholar
  16. 16.
    P.V. Shende, V.B. Labade, J.B. Gujar, B.B. Shingte, M.S. Shingare, Tetrahedron Lett. 53, 1523 (2012)CrossRefGoogle Scholar
  17. 17.
    M.R.M. Shafiee, R. Moloudi, M. Ghashang, APCBEE Procedia 1, 221 (2012)CrossRefGoogle Scholar
  18. 18.
    P. Rajput, N.J.P. Subhashini, Shivaraj, J. Sci. Res. 2, 337 (2010)CrossRefGoogle Scholar
  19. 19.
    E. Tabrizian, A. Amoozadeh, S. Rahmani, E. Imanifar, S. Azhari, M. Malmir, Chi. Chem. Lett. 26, 1278 (2015)CrossRefGoogle Scholar
  20. 20.
    M.R.M. Shafiee, R. Moloudi, Lett. Org. Chem. 8, 719 (2011)Google Scholar
  21. 21.
    R.S. Rohokale, B. Koenig, D.D. Dhavale, J. Org. Chem. 81, 7121 (2016)CrossRefGoogle Scholar
  22. 22.
    M. Kamli, Cogent Chem. 2, 1171123 (2016)Google Scholar
  23. 23.
    V. Kannan, K. Sreekumar, Mod. Res. Catal. 2, 42 (2013)CrossRefGoogle Scholar
  24. 24.
    J. Safari, S.G. Ravandi, M.B. Borujeni, J. Chem. Sci. 125, 1063 (2013)CrossRefGoogle Scholar
  25. 25.
    Z. Zarnegar, J. Safari, M.B. Borujeni, Chem. Hete. Comp. 501, 683 (2015)Google Scholar
  26. 26.
    Z.L. Min, T.Z. Yin, X.M. Hu, Asian J. Chem. 26, 7977 (2014)CrossRefGoogle Scholar
  27. 27.
    S. Mahernia, M. Adib, M. Mahdavi, M. Nosrati, Tetrahedron Lett. 55, 3844 (2014)CrossRefGoogle Scholar
  28. 28.
    A. Thangaraj, M.J. Eapen, S. Sivasanker, P. Ratnasamy, Zeolites 12, 943 (1992)CrossRefGoogle Scholar
  29. 29.
    M. Taramasso, U. S. Patent 4, 410 (1983)Google Scholar
  30. 30.
    H.F. Youssef, W.H. Hegazy, H.H. Abo-almaged, G.T. El-Bassyouni, Bioinorg. Chem. App. 12, 428121 (2015)Google Scholar
  31. 31.
    M. Opanasenko, A. Dhakshinamoorthy, M. Shamzhy, P. Nachtigall, M. Horacek, H. Garcia, J. Cejka, J. Catal. Sci. Technol. 3, 500 (2013)CrossRefGoogle Scholar
  32. 32.
    N. Wilde, M. Pelz, S.G. Gebhardt, R. Glaser, Green Chem. 17, 3378 (2015)CrossRefGoogle Scholar
  33. 33.
    M.G. Clerici, O.A. Kholdeeva, Liquid Phase Oxidation Via Heterogeneous Catalysis, Firsted (Wiley, Hoboken, 2013)CrossRefGoogle Scholar
  34. 34.
    Y. Hayashi, Chem. Sci 7, 866 (2016)CrossRefGoogle Scholar
  35. 35.
    C. Abraham, G.M. Dmitry, K. Steven, B. Timothy, D.B. Jonathan Milton, J. Solvent Extr. Ion Exch. 30, 229 (2012)CrossRefGoogle Scholar
  36. 36.
    K. Moller, T. Bein, Chem. Soc. Rev. 42, 3689 (2013)CrossRefGoogle Scholar
  37. 37.
    C.K. Banerjee, J.D. Umarye, P.R. Kanjilal, Synth. Commun. 43, 2208 (2013)CrossRefGoogle Scholar
  38. 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)CrossRefGoogle Scholar
  39. 39.
    J. Zhuaung, Z. Yan, X. Liu, X. Liu, X. Han, X. Bao, U. Mueller, Catal. Lett. 83, 1 (2002)CrossRefGoogle Scholar
  40. 40.
    S. P. Gadekar, G. T. Pawar, R. R. Magar, M. K. Lande, Polycycl. Aromat. Compd. (2017)Google Scholar
  41. 41.
    G.T. Pawar, S.P. Gadekar, B.R. Arbad, M.K. Lande, Bull. Chem. Rea. Eng. Catal. 12, 32 (2016)CrossRefGoogle Scholar
  42. 42.
    M.M. Treacy, J.B. Higgins, Collection of Simulated XRD Powder Patterns for Zeolites (Elsevier, Amsterdam, 2001), p. 236CrossRefGoogle Scholar
  43. 43.
    Y. Xue, Y. Xie, H. Wei, Y. Wen, X. Wang, B. Li, New J. Chem. 38, 4229 (2014)CrossRefGoogle Scholar
  44. 44.
    X. Wang, Y. Guo, X. Zhang, Y. Wang, H. Liu, J. Wang, J. Qiua, K.L. Yeung, Chem. Eng. J. 156, 562 (2010)CrossRefGoogle Scholar
  45. 45.
    R. Barakov, N. Shcherban, P. Yaremov, V. Solomakha, A. Yshnevskyy, V. Ilyin, J. Porous Mat. 23, 517 (2016)CrossRefGoogle Scholar
  46. 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)CrossRefGoogle Scholar
  47. 47.
    G. Ricchiardi, A. Damin, S. Bordiga, C. Lamberti, G. Spano, F. Rivetti, A. Zecchinna, J. Am. Chem. Soc. 123, 11409 (2001)CrossRefGoogle Scholar
  48. 48.
    A.C.K. Yip, F.L.Y. Lam, X. Hu, P. Li, W.K. Yuan, Ind. Eng. Chem. Res. 48, 5266 (2009)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of ChemistryDr. Babasaheb Ambedkar Marathwada UniversityAurangabadIndia

Personalised recommendations