Skip to main content
Log in

Magnetic phosphonium ionic liquid: Application as a novel dual role acidic catalyst for synthesis of 2′-aminobenzothiazolomethylnaphthols and amidoalkyl naphthols

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

Abstract

In this investigation, a novel magnetic phosphonium ionic liquid (MPIL) was designed and synthesized through a two-step process. The resulting magnetic ionic liquid was fully characterized using different techniques including Fourier-transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), derivative thermogravimetric analysis (DTG), energy-dispersive X-ray spectroscopy (EDX) and vibrating sample magnetometer (VSM). The prepared dual acidic MPIL represents brilliant catalytic performance towards the synthesis of 2′-aminobenzothiazolomethylnaphthol and amidoalkyl naphthol derivatives. Combination of magnetic, Bronsted and Lewis acid ability within a single compound is the major advantage of prepared MPIL. The present work can open up a new and promising insight in the course of rational design, synthesis and applications of task-specific multi-rule magnetic ionic liquids for various purposes.

Graphic abstract

A novel magnetic phosphonium ionic liquid promoted the synthesis of 2′-aminobenzothiazolomethylnaphthols and amidoalkyl naphthol derivatives.

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
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8

Similar content being viewed by others

References

  1. S. Hayashi, H. Hamaguchi, Chem. Lett. 33, 1590 (2004)

    CAS  Google Scholar 

  2. S. Hayashi, H. Hamaguchi, IEEE Trans. Magn. 42, 12 (2006)

    CAS  Google Scholar 

  3. E. Santos, J. Albo, A. Irabien, RSC Adv. 4, 40008 (2014)

    CAS  Google Scholar 

  4. W.-W. Hea, G.-F. Qu, Q. Zhao, X.-F. Li, Key Eng. Mater. 727, 98 (2017)

    Google Scholar 

  5. K.D. Clark, O. Nacham, J.A. Purslow, S.A. Pierson, J.L. Anderson, Anal. Chim. Acta 934, 9 (2016)

    CAS  PubMed  Google Scholar 

  6. J. Albo, E. Santos, L.A. Neves, S.P. Simeonov, C.A.M. Afonso, J.G. Crespo, A. Irabien, Sep. Purif. Technol. 97, 26 (2012)

    CAS  Google Scholar 

  7. O. Nacham, K.D. Clark, H. Yu, J.L. Anderson, Chem. Mater. 27, 923 (2015)

    CAS  Google Scholar 

  8. E. Santos, J. Albo, A. Rosatella, C.A.M. Afonso, A. Irabien, J. Chem. Technol. Biotechnol. 89, 866 (2014)

    CAS  Google Scholar 

  9. M.S. Sitze, E.R. Schreiter, E.V. Patterson, R.G. Freeman, Inorg. Chem. 40, 2298 (2001)

    CAS  PubMed  Google Scholar 

  10. J. Wang, H. Yao, Y. Nie, L. Bai, X. Zhang, J. Li, Ind. Eng. Chem. Res. 51, 3776 (2012)

    CAS  Google Scholar 

  11. R.L. Vekariya, J. Mol. Liq. 227, 44 (2017)

    CAS  Google Scholar 

  12. R.L. Vekariya, J. Disper. Sci. Technol. 38, 1594 (2017)

    CAS  Google Scholar 

  13. J. Lunagariya, A. Dhar, R.L. Vekariya, RSC Adv. 7, 5412 (2017)

    CAS  Google Scholar 

  14. R.L. Vekariya, A. Dhar, J. Lunagariya, Compos. Interface 24, 801 (2017)

    CAS  Google Scholar 

  15. R.L. Vekariya, N. Siva Kumar, Coll. Surf. A 529, 203 (2017)

    CAS  Google Scholar 

  16. L. Levi, T.J.J. Muller, Chem. Soc. Rev. 45, 2825 (2016)

    CAS  PubMed  Google Scholar 

  17. J.F.A. Filho, B.C. Lemos, A.S. de Souza, S. Pinheiro, S.J. Greco, Tetrahedron 73, 6977 (2017)

    Google Scholar 

  18. S. Garbarino, D. Ravelli, S. Protti, A. Basso, Angew. Chem. Int. Ed. 55, 15476 (2016)

    Google Scholar 

  19. R. Kakuchi, Angew. Chem. Int. Ed. 53, 46 (2014)

    CAS  Google Scholar 

  20. T. Ahmadi, G. Mohammadi Ziarani, P. Gholamzadeh, H. Mollabagher, Tetrahedron Asymmetry 28, 708 (2017)

    CAS  Google Scholar 

  21. M.J. Climent, A. Corma, S. Iborra, RSC Adv. 2, 16 (2012)

    CAS  Google Scholar 

  22. Y. Gu, Green Chem. 14, 2091 (2012)

    CAS  Google Scholar 

  23. S.K. Rout, S. Guin, J. Nath, B.K. Patel, Green Chem. 14, 2491 (2012). (and cited references within)

    CAS  Google Scholar 

  24. N. Khatun, L. Jamir, M. Ganesha, N.K. Patel, RSC Adv. 2, 11557 (2012). (and cited references within)

    CAS  Google Scholar 

  25. Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose, S. Shirato, J. Antibiot. 25, 44 (1972)

    CAS  PubMed  Google Scholar 

  26. S. Remillard, L.I. Rebhun, G.A. Howie, S.M. Kupchan, Science 189, 1002 (1975)

    CAS  PubMed  Google Scholar 

  27. J.L. Peglion, J. Vian, B. Gourment, N. Despaux, V. Audinot, M. Millan, Bioorg. Med. Chem. Lett. 7, 881 (1997)

    CAS  Google Scholar 

  28. H.S. Mosher, M.B. Frankel, M. Gregory, J. Am. Chem. Soc. 75, 5326 (1953)

    CAS  Google Scholar 

  29. G.Y. Lesher, A.R. Surrey, J. Am. Chem. Soc. 77, 636 (1955)

    CAS  Google Scholar 

  30. R.D. Clark, J.M. Caroon, A.F. Kluge, D.B. Repke, A.P. Roszkowski, A.M. Strosberg, S. Baker, S.M. Bitter, M.D. Okada, J. Med. Chem. 26, 657 (1983)

    CAS  PubMed  Google Scholar 

  31. P.K. Sahu, P.K. Sahu, D.D. Agarwal, RSC Adv. 5, 69143 (2015)

    CAS  Google Scholar 

  32. B. Adrom, M.T. Maghsoodlou, N. Hazeri, M. Lashkari, Res. Chem. Intermed. 41, 7553 (2015)

    CAS  Google Scholar 

  33. M. Seddighi, F. Shirini, M. Mamaghani, C. R. Chimie. 18, 573 (2015)

    CAS  Google Scholar 

  34. A. Hosseinian, H.R. Shaterian, Phosphorus Sulfur Silicon Relat. Elem. 187, 1056 (2012)

    CAS  Google Scholar 

  35. O. Goli-Jolodar, F. Shirini, M. Seddighi, RSC Adv. 6, 44794 (2016)

    CAS  Google Scholar 

  36. N. Nabinia, F. Shirini, H. Tajik, M. Mashhadinezhad, M. Safarpoor, N. Langarudi, J. Iran. Chem. Soc. 9, 2147 (2018)

    Google Scholar 

  37. P.K. Sahu, P.K. Sahuab, D.D. Agarwal, RSC Adv. 4, 40414 (2014)

    CAS  Google Scholar 

  38. P.K. Sahu, P.K. Sahu, D. Thavaselvam, A.M. Alafeefy, D.D. Agarwal, Med. Chem. Res. 24, 725 (2015)

    CAS  Google Scholar 

  39. P.K. Kalavagunta, P.K. Bagul, A. Jallapally, S. Kantevari, S.K. Banerjee, N. Ravirala, Eur. J. Med. Chem. 83, 344 (2014)

    CAS  PubMed  Google Scholar 

  40. H.R. Shaterian, A. Hosseinian, Sci. Iran. 21, 727 (2014)

    CAS  Google Scholar 

  41. S.B. Patil, P.R. Singh, M.P. Surpur, S.D. Samant, Ultrason. Sonochem. 14, 515 (2007)

    CAS  PubMed  Google Scholar 

  42. A. Khazaei, A.R. Moosavi-Zare, S. Firoozmand, M.R. Khodadadian, Appl. Organometal. Chem. 32, e4058 (2017)

    Google Scholar 

  43. A.S. Amarasekara, J. Nguyen, A. Razzaq, J. Polym. Res. 24, 52 (2017)

    Google Scholar 

  44. E. Soleimani, M. Zainali, Synth. Commun. 42, 1885 (2012)

    CAS  Google Scholar 

  45. S.R. Roy, A. Nijamudheen, A. Pariyar, A. Ghosh, P.K. Vardhanapu, P.K. Mandal, A. Datta, S.K. Mandal, ACS Catal. 4, 4307 (2014)

    CAS  Google Scholar 

  46. Q. Zhang, Y.-H. Gao, S.-L. Qin, H.-X. Wei, Catalysts 7, 351 (2017)

    Google Scholar 

  47. S.R. Bankar, S.N. Shelke, Res. Chem. Intermed. 44, 3507 (2018)

    CAS  Google Scholar 

  48. A. Gupta, D. Kour, V.K. Gupta, K.K. Kapoor, Tetrahedron Lett. 57, 4869 (2016)

    CAS  Google Scholar 

  49. M.A. Zolfigol, S. Baghery, A.R. Moosavi-Zare, S.M. Vahdat, J. Mol. Catal. A Chem. 409, 216 (2015)

    CAS  Google Scholar 

  50. H.R. Shaterian, H. Yarahmadi, M. Ghashang, Bioorg. Med. Chem. Lett. 18, 788 (2008)

    CAS  PubMed  Google Scholar 

  51. Q. Zhang, J. Luo, Y. Wei, Green Chem. 12, 2246 (2010)

    CAS  Google Scholar 

  52. B. Datta, M.A. Pasha, Ultrason. Sonochem. 18, 624 (2011)

    CAS  PubMed  Google Scholar 

  53. N.P. Selvam, P.T. Perumal, Tetrahedron Lett. 47, 7481 (2006)

    CAS  Google Scholar 

  54. A.R. Moosavi-Zare, M.A. Zolfigol, M. Daraei, Synletters 25, 1173 (2014)

    Google Scholar 

  55. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, A. Parhami, A. Khalafi-Nezhad, Appl. Catal. A Gen. 386, 179 (2010)

    CAS  Google Scholar 

  56. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, F. Abi, A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem-Rostami, A. Parhami, H. Torabi-Monfared, Tetrahedron 69, 212 (2013)

    CAS  Google Scholar 

  57. S. Sayyahi, A. Azin, S.J. Saghanezhad, J. Mol. Liq. 198, 30 (2014)

    CAS  Google Scholar 

  58. D.P. Narayanan, S.K. Cherikallinmel, S. Sankaran, B.N. Narayanan, J. Colloid Interface Sci. 520, 70 (2018)

    CAS  PubMed  Google Scholar 

  59. M. Yarie, M.A. Zolfigol, Y. Bayat, A. Asgari, D.A. Alonso, A. Khoshnood, RSC Adv. 6, 82842 (2016)

    CAS  Google Scholar 

  60. M.A. Zolfigol, M. Yarie, Appl. Organometal. Chem. 31, e3598 (2017)

    Google Scholar 

  61. M. Yarie, M.A. Zolfigol, S. Baghery, D.A. Alonso, A. Khoshnood, M. Kalhor, Y. Bayat, A. Asgari, New J. Chem. 41, 4431 (2017)

    CAS  Google Scholar 

  62. M.A. Zolfigol, F. Karimi, M. Yarie, M. Torabi, Appl. Organometal. Chem. 32, e4063 (2017)

    Google Scholar 

  63. M.A. Zolfigol, M. Navazeni, M. Yarie, R. Ayazi-Nasrabadi, Res. Chem. Intermed. 44, 191 (2018)

    CAS  Google Scholar 

  64. E. Kianpour, S. Azizian, M. Yarie, M.A. Zolfigol, M. Bayat, Chem. Eng. J. 295, 500 (2016)

    CAS  Google Scholar 

  65. F. Rafiee Moghadam, S. Azizian, M. Yarie, E. Kianpour, M. Bayat, M.A. Zolfigol, Chem. Eng. J. 309, 480 (2017)

    Google Scholar 

  66. F. Rafiee Moghadam, S. Azizian, M. Bayat, M. Yarie, E. Kianpour, M.A. Zolfigol, Fuel 208, 214 (2017)

    Google Scholar 

  67. A. Khazaei, M.A. Zolfigol, T. Faal-Rastegar, J. Chem. Res. 37, 617 (2013)

    CAS  Google Scholar 

  68. M. Yarie, M.A. Zolfigol, M. Saeidi-Rad, J. Mol. Liq. 249, 144 (2018)

    CAS  Google Scholar 

  69. S.M. Vahdata, M.A. Zolfigol, S. Baghery, Appl. Organometal. Chem. 30, 311 (2016)

    Google Scholar 

  70. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, E. Ghaemi, V. Khakyzadeh, Zh Asgari, A. Hasaninejad, Sci. Iran. 18, 1365 (2011)

    CAS  Google Scholar 

Download references

Acknowledgements

We thank Bu-Ali Sina University and Iran National Science Foundation (INSF) (Grant Number: 98001912), for financial support.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Meysam Yarie or Mohammad Ali Zolfigol.

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 material 1 (PDF 1032 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Torabi, M., Yarie, M., Zolfigol, M.A. et al. Magnetic phosphonium ionic liquid: Application as a novel dual role acidic catalyst for synthesis of 2′-aminobenzothiazolomethylnaphthols and amidoalkyl naphthols. Res Chem Intermed 46, 891–907 (2020). https://doi.org/10.1007/s11164-019-03996-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-03996-w

Keywords

Navigation