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Research on Chemical Intermediates

, Volume 44, Issue 7, pp 4045–4062 | Cite as

Synthesis and characterization of novel binuclear task-specific ionic liquid: an efficient and sustainable sulfonic-functionalized ionic liquid for one-pot synthesis of xanthenes

Article
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Abstract

A new binuclear sulfonic-functionalized ionic liquid was synthesized in two steps and its dual solvent-catalytic activity was studied for the synthesis of a variety of xanthenes under mild conditions. The simple experimental and sustainable procedure, good yield of the desired products within short reaction times, and recyclability of the ionic liquid are some advantages of the present strategy, and the current work shows the great importance of task-specific ionic liquids in organic synthesis.

Keywords

Binuclear sulfonic-functionalized ionic liquid Task-specific ionic liquid Dual solvent-catalyst properties Xanthene Sustainable protocol 

Notes

Acknowledgements

This work was supported by a "High Impact Research Grant" (no. RP025A/B/C-14AET) for Scientific Research from University of Malaya, Malaysia. The authors are grateful to staff members in the Analytical and Testing Center of Research House of Professor Reza and the University of Malaya for partial support.

References

  1. 1.
    A.S. Amarasekara, Chem. Rev. 116, 6133 (2016)CrossRefGoogle Scholar
  2. 2.
    D.D. Patel, J.M. Lee, Chem. Rec. 12, 329 (2012)CrossRefGoogle Scholar
  3. 3.
    X. Sun, H. Luo, S. Dai, Chem. Rev. 112, 2100 (2012)CrossRefGoogle Scholar
  4. 4.
    R.L. Vekariya, J. Mol. Liq. 227, 44 (2017)CrossRefGoogle Scholar
  5. 5.
    X. Cai, Q. Wang, Y. Liu, J. Xie, Z. Long, Y. Zhou, J. Wang, A.C.S. Sustain, Chem. Eng. 4, 4986 (2016)Google Scholar
  6. 6.
    N.G. Khaligh, Res. Chem. Intermed. 41, 5411 (2015)CrossRefGoogle Scholar
  7. 7.
    N.G. Khaligh, Polycycl. Aromat. Compd. 36, 284 (2016)CrossRefGoogle Scholar
  8. 8.
    N.G. Khaligh, Chin. J. Catal. 35, 1036 (2014)CrossRefGoogle Scholar
  9. 9.
    N.G. Khaligh, Chin. J. Catal. 35, 1497 (2014)CrossRefGoogle Scholar
  10. 10.
    R.L. Vekariya, N.S. Kumar, Coll. Surf. A 529, 203 (2017)CrossRefGoogle Scholar
  11. 11.
    R.L. Vekariya, A. Dhar, J. Lunagariya, Compos. Interface 24, 801 (2017)CrossRefGoogle Scholar
  12. 12.
    H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A Chem. 182–183, 419 (2002)CrossRefGoogle Scholar
  13. 13.
    Z.S. Qureshi, K.M. Deshmukh, B.M. Bhanage, Clean Technol. Environ. 16, 1487 (2014)CrossRefGoogle Scholar
  14. 14.
    Y. Mori, I. Fujita, H. Kawabe, K. Fujita, T. Tanaka, A. Kishimoto, Analyst 111, 1409 (1986)CrossRefGoogle Scholar
  15. 15.
    Y. Kushida, T. Nagano, K. Hanaoka, Analyst 140, 685 (2015)CrossRefGoogle Scholar
  16. 16.
    Y. Hori, K. Nakaki, M. Sato, S. Mizukami, K. Kikuchi, Angew. Chem. Int. Ed. 51, 5611 (2012)CrossRefGoogle Scholar
  17. 17.
    H.N. Hafez, M.I. Hegab, I.S. Ahmed-Farag, A.B.A. El-Gazzar, Bioorg. Med. Chem. Lett. 18, 4538 (2008)CrossRefGoogle Scholar
  18. 18.
    J.J. Omolo, M.M. Johnson, S.F. van Vuuren, C.B. De Koning, Bioorg. Med. Chem. Lett. 21, 7085 (2011)CrossRefGoogle Scholar
  19. 19.
    A.M. El-Brashy, M. El-Sayed Metwally, F.A. El-Sepai, Il Farmaco 59, 809 (2004)CrossRefGoogle Scholar
  20. 20.
    C.P. Wu, D.A. van Schalkwyk, D. Taylor, P.J. Smith, K. Chibale, Int. J. Antimicrob. Agents 26, 170 (2005)CrossRefGoogle Scholar
  21. 21.
    K. Chibale, M. Visser, D. van Schalkwyk, P.J. Smith, A. Saravanamuthu, A.H. Fairlamb, Tetrahedron 59, 2289 (2003)CrossRefGoogle Scholar
  22. 22.
    A.K. Bhattacharya, K.C. Rana, M. Mujahid, I. Sehar, A.K. Saxena, Bioorg. Med. Chem. Lett. 19, 5590 (2009)CrossRefGoogle Scholar
  23. 23.
    R. Giri, J.R. Goodell, C. Xing, A. Benoit, H. Kaur, H. Hiasa, D.M. Ferguson, Bioorg. Med. Chem. 18, 1456 (2010)CrossRefGoogle Scholar
  24. 24.
    H. Naeimi, Z.S. Nazifi, C. R. Chimie 17, 41 (2014)CrossRefGoogle Scholar
  25. 25.
    M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, E. Arzroomchilar, Bioorg. Med. Chem. Lett. 18, 436 (2008)CrossRefGoogle Scholar
  26. 26.
    B. Rajitha, B.S. Kumar, Y.T. Reddy, P.N. Reddy, N. Sreenivasulu, Tetrahedron Lett. 46, 8691 (2005)CrossRefGoogle Scholar
  27. 27.
    M.S. Patil, A.V. Palav, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 2859 (2017)CrossRefGoogle Scholar
  28. 28.
    U. Kusampally, R. Pagadala, C.R. Kamatala, Tetrahedron Lett. 58, 3316 (2017)CrossRefGoogle Scholar
  29. 29.
    N.G. Khaligh, Ultrason. Sonochem. 19, 736 (2012)CrossRefGoogle Scholar
  30. 30.
    N.G. Khaligh, Catal. Sci. Technol. 2, 2211 (2012)CrossRefGoogle Scholar
  31. 31.
    F. Shirini, N.G. Khaligh, Dyes Pigm. 95, 789 (2012)CrossRefGoogle Scholar
  32. 32.
    N.G. Khaligh, F. Shirini, Ultrason. Sonochem. 22, 397 (2015)CrossRefGoogle Scholar
  33. 33.
    D. Prasad, A. Preetam, M. Nath, C. R. Chimie 15, 675 (2012)CrossRefGoogle Scholar
  34. 34.
    M.A. Naik, D. Sachdev, A. Dubey, Catal. Commun. 11, 1148 (2010)CrossRefGoogle Scholar
  35. 35.
    A. Hassner, Synthesis of Heterocycles via Cycloadditions II (Springer, Berlin Heidelberg, 2008)CrossRefGoogle Scholar
  36. 36.
    N.G. Khaligh, J. Mol. Catal. A Chem. 349, 63 (2011)CrossRefGoogle Scholar
  37. 37.
    N.G. Khaligh, Catal. Sci. Technol. 2, 1633 (2012)CrossRefGoogle Scholar
  38. 38.
    N.G. Khaligh, Chin. Chem. Lett. 26, 26 (2015)CrossRefGoogle Scholar
  39. 39.
    N.G. Khaligh, Monatsh. Chem. 145, 1643 (2014)CrossRefGoogle Scholar
  40. 40.
    N.G. Khaligh, Monatsh. Chem. 146, 321 (2015)CrossRefGoogle Scholar
  41. 41.
    N.G. Khaligh, Polycycl. Arom. Compd. 35, 428 (2015)CrossRefGoogle Scholar
  42. 42.
    G.H. Silver, J.L. Wood, Trans. Faraday Soc. 60, 5 (1964)CrossRefGoogle Scholar
  43. 43.
    R. Ramasamy, J. Appl. Spec. 80, 492 (2013)CrossRefGoogle Scholar
  44. 44.
    R. Ramasamy, Arm. J. Phys. 8, 51 (2015)Google Scholar
  45. 45.
    V. Krishnakumar, R. Ramasamy, Indian J. Pure Appl. Phys. 40, 252 (2002)Google Scholar
  46. 46.
    N.P.G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures (Wiley, New York, 1994)Google Scholar
  47. 47.
    S.M. Chackalackal, F.E. Stafford, J. Am. Chem. Soc. 88, 4815 (1966)CrossRefGoogle Scholar
  48. 48.
    R.T. Conley, Infrared Spectroscopy (Allyn and Bacon Inc., Boston, 1966)Google Scholar
  49. 49.
    K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds (Wiley, N.Y., 1986)Google Scholar
  50. 50.
    C.N.R. Rao, Can. J. Chem. 42, 36 (1964)CrossRefGoogle Scholar
  51. 51.
    L. Jurd, J. Org. Chem. 31, 1639 (1966)CrossRefGoogle Scholar
  52. 52.
    Y.L. Li, X.S. Wang, D.Q. Shi, S.J. Tu, Y. Zhang, Acta Cryst. E60, o1439 (2004)Google Scholar
  53. 53.
    K. Venkatesan, S.S. Pujari, R.J. Lahoti, K.V. Srinivasan, Ultrason. Sonochem. 15, 548 (2008)CrossRefGoogle Scholar
  54. 54.
    A. Ilangovan, S. Muralidhara, P. Sakthivel, S. Malayappasamy, S. Karuppusamy, M.P. Kaushik, Tetrahedron Lett. 54, 491 (2013)CrossRefGoogle Scholar
  55. 55.
    S. Kokkirala, N.M. Sabbavarapu, V.D.N. Yadavalli, Eur. J. Chem. 2, 272 (2011)CrossRefGoogle Scholar
  56. 56.
    G.H. Mahdavinia, M.A. Bigdeli, Y. Saeidi, Hayeniaz. Chin. Chem. Lett. 20, 539 (2009)CrossRefGoogle Scholar
  57. 57.
    F. Shirini, N.G. Khaligh, G.H. Imanzadeh, P.G. Ghasem-Abadi, Chin. Chem. Lett. 23, 1145 (2012)CrossRefGoogle Scholar
  58. 58.
    A. Kumar, S. Sharma, R.A. Maurya, J. Sarkar, J. Comb. Chem. 12, 20 (2010)CrossRefGoogle Scholar
  59. 59.
    J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 4777 (2009)CrossRefGoogle Scholar
  60. 60.
    G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron 65, 7129 (2009)CrossRefGoogle Scholar
  61. 61.
    A.C. Flores, E.A. Flores, E. Hernández, L.V. Castro, A. García, F. Alvarez, F.S. Vázquez, J. Mol. Liq. 196, 249 (2014)CrossRefGoogle Scholar
  62. 62.
    M. Krannich, F. Heym, A. Jess, J. Chem. Eng. Data 61, 1162 (2016)CrossRefGoogle Scholar
  63. 63.
    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
  64. 64.
    H. Wu, X. Chen, Y. Wan, H. Xin, H. Xu, C. Yue, L. Pang, R. Ma, Synth. Commun. 39, 3762 (2009)CrossRefGoogle Scholar
  65. 65.
    B. Maleki, E. Akbarzadeh, S. Babaee, Dyes Pigments 123, 222 (2015)CrossRefGoogle Scholar
  66. 66.
    H. Singh, S. Kumari, J.M. Khurana, Chin. Chem. Lett. 25, 1336 (2014)CrossRefGoogle Scholar
  67. 67.
    F. Shirini, A. Yahyazadeh, K. Mohammadi, Chin. Chem. Lett. 25, 341 (2014)CrossRefGoogle Scholar
  68. 68.
    M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, S.B. Azimi, Z. Asgari, A. Hasaninejad, C. R. Chimie 15, 719 (2012)CrossRefGoogle Scholar
  69. 69.
    K. Gong, D. Fang, H.L. Wang, X.L. Zhou, Z.L. Liu, Dyes Pigm. 80, 30 (2009)CrossRefGoogle Scholar
  70. 70.
    A. Amoozadeh, S. Rahmani, J. Mol. Catal. A: Chem. 396, 96 (2015)CrossRefGoogle Scholar

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

Authors and Affiliations

  1. 1.Research House of Professor RezaEducation GuilanRashtIran
  2. 2.Nanotechnology and Catalysis Research Center, 3rd Floor, Block A, Institute of Postgraduate StudiesUniversity of MalayaKuala LumpurMalaysia

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