Skip to main content
SpringerLink
Log in

Triethanolamine lactate-supported nanomagnetic cellulose: a green and efficient catalyst for the synthesis of pyrazolo[3,4-b]quinolines and theoretical study

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

Abstract

A novel nanomagnetic catalyst has been synthesized by immobilization of triethanolamine lactate cellulose with Fe3O4 NPs. The prepared catalyst has been used as an efficient and recoverable catalyst for the regioselective synthesis of pyrazolo quinolones by the three-component reaction of dimedone, 5-amino pyrazolone and aromatic aldehydes in ultrasound condition. This economical catalyst provides high yields of products, short experimental time and easy workup for green synthesis of pyrazolo[3,4-b]quinolone compounds. Theoretical studies have been employed to investigate the reaction mechanism by using the B3LYP/6-311G method. Electronic parameters of all components have been determined in order to reorganize the role of components in the reaction mechanism.

Graphic abstract

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.
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. X.-L. Sun, J.C. Zheng, Y. Tang, Pure Appl. Chem. 82, 625 (2010)

    CAS  Google Scholar 

  2. W.R. Vaughan, Chem. Rev. 43, 447 (1948)

    CAS  PubMed  Google Scholar 

  3. H.W. Heine, R. Henrie, L. Heitz, S.R. Kovvali, J. Org. Chem. 39, 3187 (1974)

    CAS  Google Scholar 

  4. T. Sheradsky, R. Moshenberg, J. Org. Chem. 51, 3123 (1986)

    CAS  Google Scholar 

  5. C. Turk, J. Svete, B. Stanovnik, L. Golič, S. Golič-Grdadolnik, A. Golobič, L. Selič, Helv. Chim. Acta 84, 146 (2001)

    CAS  Google Scholar 

  6. G. Heinisch, H. Frank, in Progress in Medicinal Chemistry, ed. by G.P. Ellis and G.B. West (Elsevier, Amsterdam, 1990), pp. 1–49

  7. M. Zahedifar, B. Pouramiri, F. Ezzati Ghadi, R. Razavi, A. Ramzani Ghara, Mol. Divers. (2019). https://doi.org/10.1007/s11030-019-10022-z

  8. A.H. El-Wahab, Z.I. Al-Fifi, A.H. Bedair, F.M. Ali, A.H. Halawa, A.M. El-Agrody, Molecules 16, 307 (2011)

    PubMed  PubMed Central  Google Scholar 

  9. G. Ouyang, X.-J. Cai, Z. Chen, B.-A. Song, P.S. Bhadury, S. Yang, L.-H. Jin, W. Xue, D.-Y. Hu, S. Zeng, J. Agric. Food. Chem. 56, 10160 (2008)

    CAS  PubMed  Google Scholar 

  10. H.A. Saad, N.A. Osman, A.H. Moustafa, Molecules 16, 10187 (2011)

    CAS  PubMed  PubMed Central  Google Scholar 

  11. H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 6, 3321 (2000)

    PubMed  Google Scholar 

  12. A. Nefzi, J.M. Ostresh, R.A. Houghten, Chem. Rev. 97, 449 (1997)

    CAS  PubMed  Google Scholar 

  13. L.A. Thompson, Curr. Opin. Chem. Biol. 4, 324 (2000)

    CAS  PubMed  Google Scholar 

  14. A. Dömling, Curr. Opin. Chem. Biol. 6, 306 (2002)

    PubMed  Google Scholar 

  15. R. Vijayaraghavan, D.R. MacFarlane, Aust. J. Chem. 57, 129 (2004)

    CAS  Google Scholar 

  16. Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem., Int. Ed. 34, 2698 (1996)

  17. M.A. Klingshirn, R.D. Rogers, K.H. Shaughnessy, J. Organomet. Chem. 690, 3620 (2005)

    CAS  Google Scholar 

  18. M. Johansson, A.A. Lindén, J.-E. Bäckvall, J. Organomet. Chem. 690, 3614 (2005)

    CAS  Google Scholar 

  19. A. Serbanovic, L.C. Branco, M. Nunes da Ponte, C.A.M. Afonso, J. Organomet. Chem. 690, 3600 (2005)

    CAS  Google Scholar 

  20. D. Zhao, Y. Liao, Z. Zhang, Clean-Soil. Air, Water. 35, 42 (2007)

    Google Scholar 

  21. O.G. da Silva, E.C.F. da Silva, M.G. Fonseca, L.N. Arakaki, C. Airoldi, J. Colloid Interface Sci. 302, 485 (2006)

    CAS  PubMed  Google Scholar 

  22. K. Ghandi, Green Sustain. Chem. 4, 2160 (2014)

    Google Scholar 

  23. A. Akbari, N. Arsalani, M. Amini, E. Jabbari, J. Mol. Catal. A Chem. 414, 47 (2016)

    CAS  Google Scholar 

  24. A.E. Aksoylu, M. Madalena, A. Freitas, M.F.R. Pereira, J.L. Figueiredo, Carbon 39, 175 (2001)

    CAS  Google Scholar 

  25. Z. Yu, X. Min, F. Li, Q. Chen, D. Yin, Y. Peng, Mater. Technol. 33, 612 (2018)

    CAS  Google Scholar 

  26. M.-F. Huang, J.-G. Yu, X.-F. Ma, Polymer 45, 7017 (2004)

    CAS  Google Scholar 

  27. K. Molvinger, F. Quignard, D. Brunel, M. Boissière, J.-M. Devoisselle, Chem. Mater. 16, 3367 (2004)

    CAS  Google Scholar 

  28. S. Rogalsky, J.-F. Bardeau, S. Makhno, N. Babkina, O. Tarasyuk, T. Cherniavska, I. Orlovska, N. Kozyrovska, O. Brovko, Polymer 142, 183 (2018)

    CAS  Google Scholar 

  29. B.B.F. Mirjalili, F. Aref, Res. Chem. Intermed. 44, 4519 (2018)

    CAS  Google Scholar 

  30. R. Shojaei, M. Zahedifar, P. Mohammadi, K. Saidi, H. Sheibani, J. Mol. Struct. 1178, 401 (2019)

    CAS  Google Scholar 

  31. M. Zahedifar, A. Es-haghi, R. Zhiani, S.M. Sadeghzadeh, RSC Adv. 9, 6494 (2019)

    CAS  Google Scholar 

  32. M. Zahedifar, M. Shirani, A. Akbari, N. Seyedi, Cellulose 26, 6797 (2019)

    CAS  Google Scholar 

  33. M. Zahedifar, R. Zhiani, S.M. Sadeghzadeh, F. Shamsa, New J. Chem. 43, 4489 (2019)

    CAS  Google Scholar 

  34. R. Zhiani, S.M. Saadati, M. Zahedifar, S.M. Sadeghzadeh, Catal. Lett. 148, 2487 (2018)

    CAS  Google Scholar 

  35. A.D. Becke, Phys. Rev. A. 38, 3098 (1988)

    CAS  Google Scholar 

  36. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, J. Phys. Chem. 98, 11623 (1994)

    CAS  Google Scholar 

  37. R.A. Gaussian 09, G.W.T. M. J. Frisch, H. B. Schlegel, G. E. Scuseria, J.R.C. M. A. Robb, G. Scalmani, V. Barone, B. Mennucci, H.N. G. A. Petersson, M. Caricato, X. Li, H. P. Hratchian, J.B. A. F. Izmaylov, G. Zheng, J. L. Sonnenberg, M. Hada, K.T. M. Ehara, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, O.K. Y. Honda, H. Nakai, T. Vreven, J. A. Montgomery, Jr., F.O. J. E. Peralta, M. Bearpark, J. J. Heyd, E. Brothers, V.N.S. K. N. Kudin, R. Kobayashi, J. Normand, A.R. K. Raghavachari, J. C. Burant, S. S. Iyengar, J. Tomasi, N.R. M. Cossi, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, C.A. V. Bakken, J. Jaramillo, R. Gomperts, R. E. Stratmann, A.J.A. O. Yazyev, R. Cammi, C. Pomelli, J. W. Ochterski, K.M. R. L. Martin, V. G. Zakrzewski, G. A. Voth, J.J.D. P. Salvador, S. Dapprich, A. D. Daniels, J.B.F. O. Farkas, J. V. Ortiz, J. Cioslowski, G. and D. J. Fox, Inc., Wallingford CT, 2009

  38. D.W. Smith, O.W. Day, J. Chem. Phys. 62, 113 (1975)

    CAS  Google Scholar 

  39. A. Bhowmick, D. Weatherman, P.P. Kundu, A.G. Sykes, Adv. Polym. Tech. 37, 235 (2016)

    Google Scholar 

  40. W. Lan, C.-F. Liu, F.-X. Yue, R.-C. Sun, J.F. Kennedy, Carbohydr. Polym. 86, 672 (2011)

    CAS  Google Scholar 

  41. X. Wang, P. Hu, F. Xue, Y. Wei, Carbohydr. Polym. 114, 476 (2014)

    CAS  PubMed  Google Scholar 

  42. M. Zahedifar, P. Mohammadi, H. Sheibani, Lett. Org. Chem. 14, 315 (2017)

    CAS  Google Scholar 

  43. M. Zahedifar, R. Shojaei, H. Sheibani, Res. Chem. Intermed. 44, 873(2018)

    CAS  Google Scholar 

  44. S.J. Basha, S.P.V. Chamundeeswari, S. Muthu, B.R. Raajaraman, J. Mol. Liq. 296, 111787 (2019)

    CAS  Google Scholar 

  45. G. Singh, J. Sindhu, V. Kumar, V. Sharma, S.K. Sharma, S.K. Mehta, M.H. Mahnashi, A. Umar, R. Kataria, J. Mol. Liq. 296, 111814 (2019)

    CAS  Google Scholar 

  46. M. Zahedifar, H. Sheibani, V. Saheb, Synlett 29, 1836 (2018)

    CAS  Google Scholar 

  47. M. Zahedifar, R. Razavi, H. Sheibani, J. Mol. Struct. 1125, 730 (2016)

    CAS  Google Scholar 

Download references

Acknowledgements

The authors express appreciation to the University of Jiroft Faculty Research Committee and Jiroft University of Medical Science for supporting this investigation.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Jiroft, 7867161167, Jiroft, Iran

    Mahboobeh Zahedifar & Razieh Razavi

  2. Student Research Committee, Jiroft University of Medical Sciences, Jiroft, Iran

    Behjat Pouramiri

Authors
  1. Mahboobeh Zahedifar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Behjat Pouramiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Razieh Razavi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mahboobeh Zahedifar.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 4958 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zahedifar, M., Pouramiri, B. & Razavi, R. Triethanolamine lactate-supported nanomagnetic cellulose: a green and efficient catalyst for the synthesis of pyrazolo[3,4-b]quinolines and theoretical study. Res Chem Intermed 46, 2749–2765 (2020). https://doi.org/10.1007/s11164-020-04117-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04117-8

Keywords

Search

Navigation