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A caffeine-based ionic liquid as a novel and eco-friendly catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions

  • Masoumeh Salami
  • Ali EzabadiEmail author
Article
  • 18 Downloads

Abstract

A new Brönsted acidic ionic liquid has been synthesized using caffeine and p-toluenesulfonic acid as precursors. The IL was fully characterized by FT-IR, 1H NMR, 13C NMR, MS, elemental analysis, as well as Hammett acidity function. The prepared reagent is efficiently able to catalyze the synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions. Various advantages associated with this method include novelty and easy preparation of catalyst, simple work-up procedure and purification, short reaction times, high product yields, and easy recovery and reusability of the catalyst.

Keywords

Ionic liquid Caffeine p-Toluenesulfonic acid 1,8-Dioxo-octahydroxanthenes Solvent-free conditions 

Notes

References

  1. 1.
    D.R. Bhatt, K.C. Maheria, J.K. Parikh, RSC Adv. 5, 12139 (2015)CrossRefGoogle Scholar
  2. 2.
    B. Wang, L. Qin, T. Mu, Z. Xue, G. Gao, Chem. Rev. 117, 7113 (2017)CrossRefGoogle Scholar
  3. 3.
    A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq. 186, 63 (2013)CrossRefGoogle Scholar
  4. 4.
    S.P. Satasia, P.N. Kalaria, D.K. Raval, J. Mol. Catal. A: Chem. 391, 41 (2014)CrossRefGoogle Scholar
  5. 5.
    H.G. Alvim, G.A. Bataglion, L.M. Ramos, A.L. de Oliveira, H.C. de Oliveira, M.N. Eberlin, J.L. de Macedo, W.A. da Silva, B.A. Neto, Tetrahedron 70, 3306 (2014)CrossRefGoogle Scholar
  6. 6.
    A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, Z. Asgari, M. Shekouhy, A. Zare, A. Hasaninejad, RSC Adv. 2, 8010 (2012)CrossRefGoogle Scholar
  7. 7.
    D.-Q. Xu, J. Wu, S.-P. Luo, J.-X. Zhang, J.-Y. Wu, X.-H. Du, Z.-Y. Xu, Green Chem. 11, 1239 (2009)CrossRefGoogle Scholar
  8. 8.
    A.R. Moosavi-Zare, M.A. Zolfigol, V. Khakyzadeh, C. Böttcher, M.H. Beyzavi, A. Zare, A. Hasaninejad, R. Luque, J. Mater. Chem. A. 2, 770 (2014)CrossRefGoogle Scholar
  9. 9.
    M. Yarie, M.A. Zolfigol, M. Saeidi-Rad, J. Mol. Liq. 249, 144 (2018)CrossRefGoogle Scholar
  10. 10.
    S.A. Ghumro, S. Saleem, M. al-Rashida, N. Iqbal, R.D. Alharthy, S. Ahmed, S.T. Moin, A. Hameed, RSC Adv. 7, 34197 (2017)CrossRefGoogle Scholar
  11. 11.
    Suresh, J.S. Sandhu, Green Chem. Lett. Rev. 4, 289 (2011)CrossRefGoogle Scholar
  12. 12.
    J. Poupelin, G. Saintruf, R. Lacroix, G. Narcisse, O. Foussardblanpin, G. Uchidaernouf, Eur. J. Med. Chem. 13, 381 (1978)Google Scholar
  13. 13.
    R. Lambert, J. Martin, J. Merrett, K. Parkes, G. Thomas, in Chem. Abstr., p. 212377y (1997)Google Scholar
  14. 14.
    R.-M. Ion, A. Planner, K. Wiktorowicz, D. Frackowiak, Acta Biochim. Pol. 45, 833 (1998)Google Scholar
  15. 15.
    V.R. Narayana, Z. Pudukulathan, R. Varala, Org. Commun. 6, 110 (2013)Google Scholar
  16. 16.
    M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes Pigm. 76, 836 (2008)CrossRefGoogle Scholar
  17. 17.
    A.N. Dadhania, V.K. Patel, D.K. Raval, J. Saudi. Chem. Soc. 21, S163 (2017)CrossRefGoogle Scholar
  18. 18.
    S.H. Banakar, M.G. Dekamin, A. Yaghoubi, New J. Chem. 42, 14246 (2018)CrossRefGoogle Scholar
  19. 19.
    M. Nasr-Esfahani, Z. Rafiee, H. Kashi, Phosphorus, Sulfur, Silicon, Relat. Elem. 191, 790 (2016)CrossRefGoogle Scholar
  20. 20.
    A. Ilangovan, S. Muralidharan, P. Sakthivel, S. Malayappasamy, S. Karuppusamy, M. Kaushik, Tetrahedron Lett. 54, 491 (2013)CrossRefGoogle Scholar
  21. 21.
    F.S. Arbosara, F. Shirini, M. Abedini, H.F. Moafi, J. Nanostructure Chem. 5, 55 (2015)CrossRefGoogle Scholar
  22. 22.
    F. Shirini, N.G. Khaligh, Dyes Pigm. 95, 789 (2012)CrossRefGoogle Scholar
  23. 23.
    H.Y. Lue, J.J. Li, Z.H. Zhang, Appl. Organomet. Chem. 23, 165 (2009)CrossRefGoogle Scholar
  24. 24.
    Z. Zhou, X. Deng, J. Mol. Catal. A: Chem. 367, 99 (2013)CrossRefGoogle Scholar
  25. 25.
    A. Gharib, L. Vojdani Fard, N. Noroozi Pesyan, M. Roshani, Chem. J. 1, 58 (2015)Google Scholar
  26. 26.
    G.R. Chaudhary, P. Bansal, N. Kaur, S. Mehta, RSC Adv. 4, 49462 (2014)CrossRefGoogle Scholar
  27. 27.
    B. Maleki, A. Davoodi, M.V. Azghandi, M. Baghayeri, E. Akbarzadeh, H. Veisi, S.S. Ashrafi, M. Raei, New J. Chem. 40, 1278 (2016)CrossRefGoogle Scholar
  28. 28.
    P.J. Das, J. Das, RSC Adv. 5, 11745 (2015)CrossRefGoogle Scholar
  29. 29.
    A. Ilangovan, S. Malayappasamy, S. Muralidharan, S. Maruthamuthu, Chem. Cent. J. 5, 81 (2011)CrossRefGoogle Scholar
  30. 30.
    H. Ulusal, G. Fındıkkıran, O. Demirkol, D. Akbaşlar, E.S. Giray, J. Supercrit. Fluid. 105, 146 (2015)CrossRefGoogle Scholar
  31. 31.
    K. Gong, H. Wang, S. Wang, Y. Wang, J. Chen, Chin. J. Catal. 36, 1249 (2015)CrossRefGoogle Scholar
  32. 32.
    A. Thakur, A. Sharma, A. Sharma, Synth. Commun. 46, 1766 (2016)CrossRefGoogle Scholar
  33. 33.
    A. Rajini, C. Suman, A. Ajay Kumar, S. Suresh, N. Venkatathri, Synth. Commun. 46, 1671 (2016)CrossRefGoogle Scholar
  34. 34.
    Z.-H. Zhang, Y.-H. Liu, Catal. Commun. 9, 1715 (2008)CrossRefGoogle Scholar
  35. 35.
    K. Venkatesan, S.S. Pujari, R. Lahoti, K. Srinivasan, Ultrason. Sonochem. 15, 548 (2008)CrossRefGoogle Scholar
  36. 36.
    A.M. Ghasemzadeh, J. Safaei-Ghomi, S. Zahedi, J. Serb. Chem. Soc. 78, 769 (2013)CrossRefGoogle Scholar
  37. 37.
    G.K. Verma, K. Raghuvanshi, R.K. Verma, P. Dwivedi, M. Singh, Tetrahedron 67, 3698 (2011)CrossRefGoogle Scholar
  38. 38.
    D. Fang, J.M. Yang, Z.L. Liu, J. Heterocycl. Chem. 48, 468 (2011)CrossRefGoogle Scholar
  39. 39.
    F. Shirini, M.S.N. Langarudi, M. Seddighi, O.G. Jolodar, Res. Chem. Intermed. 41, 8483 (2015)CrossRefGoogle Scholar
  40. 40.
    S. Nazari, M. Keshavarz, B. Karami, N. Iravani, M. Vafaee-Nezhad, Chin. Chem. Lett. 25, 317 (2014)CrossRefGoogle Scholar
  41. 41.
    A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq. 167, 69 (2012)CrossRefGoogle Scholar
  42. 42.
    H. Emtiazi, M.A. Amrollahi, Rev. Roum. Chim. 62, 43 (2017)Google Scholar
  43. 43.
    S. Samantaray, P. Kar, G. Hota, B.G. Mishra, Ind. Eng. Chem. Res. 52, 5862 (2013)CrossRefGoogle Scholar
  44. 44.
    M. Kidwai, A. Jain, Appl. Organomet. Chem. 26, 528 (2012)CrossRefGoogle Scholar
  45. 45.
    M.T. Maghsoodlou, S.M. Habibi-Khorassani, Z. Shahkarami, N. Maleki, M. Rostamizadeh, Chin. Chem. Lett. 21, 686 (2010)CrossRefGoogle Scholar
  46. 46.
    A. Bamoniri, B.B.F. Mirjalili, S. Fouladgar, Polycyclic Aromat. Compd. 37, 345 (2017)CrossRefGoogle Scholar
  47. 47.
    T. Lohar, A. Kumbhar, M. Barge, R. Salunkhe, J. Mol. Liq. 224, 1102 (2016)CrossRefGoogle Scholar
  48. 48.
    M. Abedini, F. Shirini, J.M.-A. Omran, M. Seddighi, O. Goli-Jolodar, Res. Chem. Intermed. 42, 4443 (2016)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceIslamic Azad University, Central Tehran BranchTehranIran

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