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Simple protic ionic liquid [Et3NH][HSO4] as a proficient catalyst for facile synthesis of biscoumarins

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Abstract

We have explored a number of protic ionic liquids (PILs) as a catalyst for the synthesis of biscoumarins by condensation of 4-hydroxycoumarin with an aromatic aldehyde. Methylimidazolium- and triethylammonium-based PILs were synthesized by simple neutralization reaction with protic acids. Triethylammonium hydrogen sulfate [Et3NH][HSO4] was found to be the best among the studied PILs concerning the yield of products and reaction time period. Different biscoumarin derivatives were synthesized based on 4-hydroxycoumarin and various substituted aromatic aldehydes at optimum reaction conditions. Obtained products were separated just by simple filtration. The facile method does not require additional purification for formed products. The catalyst has shown better yields along with outstanding recyclability, providing an environmental benign protocol for the synthesis of biscoumarin derivatives.

Graphical Abstract

Screening of simple protic ionic liquids as a catalyst in the synthesis of biscoumarins, out of which [Et3NH][HSO4] was found to be best among the studied PILs.

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References

  1. N.V. Plechkova, K.R. Seddon, Chem. Soc. Rev. 37, 123 (2008)

    Article  CAS  Google Scholar 

  2. T. Welton, Chem. Rev. 99, 2071 (1999)

    Article  CAS  Google Scholar 

  3. S. Zhu, R. Chen, Y. Wu, Q. Chen, X. Zhang, Z. Yu, Chem. Biochem. Eng. Q. 23, 207 (2009)

    CAS  Google Scholar 

  4. R. Sheldon, Chem. Commun. 2399 (2001)

    Article  Google Scholar 

  5. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008)

    Article  CAS  Google Scholar 

  6. A.R. Hajipour, F. Rafiee, Org. Prep. Proced. Int. 42, 285 (2010)

    Article  CAS  Google Scholar 

  7. T.L. Greaves, C.J. Drummond, Chem. Rev. 108, 206 (2008)

    Article  CAS  Google Scholar 

  8. P.P. Salvi, A.M. Mandhare, A.S. Sartape, D.K. Pawar, S.H. Han, S.S. Kolekar, C. R. Chim. 14, 883 (2011)

    Article  CAS  Google Scholar 

  9. M. Picquet, I. Tkatchenko, I. Tommasi, P. Wasserscheid, J. Zimmermann, Adv. Synth. Catal. 345, 959 (2003)

    Article  CAS  Google Scholar 

  10. K.E. Johnson, R.M. Pagni, J. Bartmess, Monatsh. Chem. 138, 1077 (2007)

    Article  CAS  Google Scholar 

  11. B. Tamami, A. Sardarian, E. Ataollahi, Turk. J. Chem. 40, 422 (2016)

    Article  CAS  Google Scholar 

  12. S.A. Siddiqui, T.M. Potewar, R.J. Lahoti, K.V. Srinivasan, Synthesis, 2849 (2006)

  13. S.S. Palimkar, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Org. Chem. 68, 9371 (2003)

    Article  CAS  Google Scholar 

  14. Z. Du, Z. Li, S. Guo, J. Zhang, L. Zhu, Y. Deng, J. Phys. Chem. B 109, 19542 (2005)

    Article  CAS  Google Scholar 

  15. Z. Fei, D. Zhao, T.J. Geldbach, R. Scopelliti, P.J. Dyson, Chem. Eur. J. 10, 4886 (2004)

    Article  CAS  Google Scholar 

  16. Z. Duan, Y. Gu, J. Zhang, L. Zhu, Y. Deng, J. Mol. Catal. A: Chem. 250, 163 (2006)

    Article  CAS  Google Scholar 

  17. J. Gui, H. Ban, X. Cong, X. Zhang, Z. Hu, Z. Sun, J. Mol. Catal. A: Chem. 225, 27 (2005)

    Article  CAS  Google Scholar 

  18. C. Wang, W. Zhao, H. Li, L. Guo, Green Chem. 11, 843 (2009)

    Article  Google Scholar 

  19. A.G. Ying, H.D. Liang, R.H. Zheng, C.H. Ge, H.J. Jiang, C.L. Wu, Res. Chem. Intermed. 37, 579 (2011)

    Article  CAS  Google Scholar 

  20. R.V. Hangarge, D.V. Jarikote, M.S. Shingare, Green Chem. 4, 266 (2002)

    Article  CAS  Google Scholar 

  21. S. Rezayati, F. Sheikholeslami-Farahani, F. Rostami-Charati, S.A.S. Abad, Res. Chem. Intermed. 42, 4097 (2016)

    Article  CAS  Google Scholar 

  22. G. Karthikeyan, P.T. Perumal, Can. J. Chem. 83, 1746 (2005)

    Article  CAS  Google Scholar 

  23. Z.Y. Yu, Q.S. Fang, J. Zhou, Z.B. Song, Res. Chem. Intermed. 42, 2035 (2016)

    Article  CAS  Google Scholar 

  24. E. Janus, I. Goc-Maciejewska, M. Łożyński, J. Pernak, Tetrahedron Lett. 47, 4079 (2006)

    Article  CAS  Google Scholar 

  25. D. Patil, D. Chandam, A. Mulik, P. Patil, S. Jagadale, R. Kant, V. Gupta, M. Deshmukh, Catal. Lett. 144, 949 (2014)

    Article  CAS  Google Scholar 

  26. G. Zhao, T. Jiang, H. Gao, B. Han, J. Huang, D. Sun, Green Chem. 6, 75 (2004)

    Article  CAS  Google Scholar 

  27. H.-P. Zhu, F. Yang, J. Tang, M.-Y. He, Green Chem. 5, 38 (2003)

    Article  CAS  Google Scholar 

  28. R. Zheng, X. Wang, H. Xu, J. Du, Synth. Commun. 36, 1503 (2006)

    Article  CAS  Google Scholar 

  29. S. Guo, Z. Du, S. Zhang, D. Li, Z. Li, Y. Deng, Green Chem. 8, 296 (2006)

    Article  CAS  Google Scholar 

  30. J. Li, Y.-P. Sui, J.-J. Xin, X.-L. Du, J.-T. Li, H.-R. Huo, H. Ma, W.-H. Wang, H.-Y. Zhou, H.-D. Zhan, Z.-J. Wang, C. Li, F. Sui, X. Li, Bioorg. Med. Chem. Lett. 25, 5520 (2015)

    Article  CAS  Google Scholar 

  31. J. Li, Z. Hou, F. Li, Z.-D. Zhang, Y. Zhou, X.-X. Luo, M.-K. Li, J. Mol. Struct. 1075, 509 (2014)

    Article  CAS  Google Scholar 

  32. Y.-P. Sui, H.-R. Huo, J.-J. Xin, J. Li, X.-J. Li, X.-L. Du, H. Ma, H.-Y. Zhou, H.-D. Zhan, Z.-J. Wang, C. Li, F. Sui, M.-K. Li, Molecules 20, 17614 (2015)

    Article  CAS  Google Scholar 

  33. J.-J. Xin, J. Li, Z.-D. Zhang, X.-B. Hu, M.-K. Li, J. Mol. Struct. 1084, 200 (2015)

    Article  CAS  Google Scholar 

  34. K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Z. Ullah, M.I. Choudhary, A. Rahman, S. Perveen, Bioorg. Med. Chem. 12, 1963 (2004)

    Article  CAS  Google Scholar 

  35. K.M. Khan, F. Rahim, A. Wadood, N. Kosar, M. Taha, S. Lalani, A. Khan, M.I. Fakhri, M. Junaid, W. Rehman, M. Khan, S. Perveen, M. Sajid, M.I. Choudhary, Eur. J. Med. Chem. 81, 245 (2014)

    Article  CAS  Google Scholar 

  36. Z.N. Siddiqui, M.T.N. Musthafa, A. Ahmad, A.U. Khan, Arch. Pharm. 344, 394 (2011)

    Article  CAS  Google Scholar 

  37. I. Kostova, G. Momekov, Eur. J. Med. Chem. 41, 717 (2006)

    Article  CAS  Google Scholar 

  38. A. Das Gupta, S. Samanta, R. Mondal, A.K. Mallik, Bull. Korean Chem. Soc. 33, 4239 (2012)

    Article  CAS  Google Scholar 

  39. M. Kidwi, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 268, 76 (2007)

    Article  Google Scholar 

  40. J.N. Sangshetti, N.D. Kokare, D.B. Shinde, Green Chem. Lett. Rev. 2, 233 (2009)

    Article  CAS  Google Scholar 

  41. K. Tabatabaeian, H. Heidari, A. Khorshidi, M. Mamaghani, N.O. Mahmoodi, J. Serb. Chem. Soc. 77, 407 (2012)

    Article  CAS  Google Scholar 

  42. F. Shirini, M. Abedini, S.A. Kiaroudi, Phosphorus, Sulfur Silicon Relat. Elem. 189, 1279 (2014)

    Article  CAS  Google Scholar 

  43. B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 4343 (2012)

    Article  CAS  Google Scholar 

  44. A.R. Kiasat, L. Hemat-Alian, Res. Chem. Intermed. 41, 873 (2015)

    Article  CAS  Google Scholar 

  45. J. Albadi, A. Mansournezhad, S. Salehnasab, Res. Chem. Intermed. 41, 5713 (2015)

    Article  CAS  Google Scholar 

  46. M. Nikpassand, L.Z. Fekri, L. Karimian, M. Rassa, Curr. Org. Synth. 12, 358 (2015)

    Article  CAS  Google Scholar 

  47. R. Rezaei, M.R. Sheikhi, Res. Chem. Intermed. 41, 1283 (2015)

    Article  CAS  Google Scholar 

  48. J.M. Khurana, A. Lumb, A. Chaudhary, B. Nand, J. Heterocycl. Chem. 51, 1747 (2014)

    Article  CAS  Google Scholar 

  49. J.M. Khurana, S. Kumar, Monatsh. Chem. 141, 561 (2010)

    Article  CAS  Google Scholar 

  50. K.P. Boroujeni, P. Ghasemi, Z. Rafienia, Monatsh. Chem. 145, 1023 (2014)

    Article  Google Scholar 

  51. W. Li, Y. Wang, Z. Wang, L. Dai, Y. Wang, Catal. Lett. 141, 1651 (2011)

    Article  CAS  Google Scholar 

  52. A. Tzani, A. Douka, A. Papadopoulos, E.A. Pavlatou, E. Voutsas, A. Detsi, ACS Sustain. Chem. Eng. 1, 1180 (2013)

    Article  CAS  Google Scholar 

  53. M.A. Zolfigol, A.R. Moosavi-Zare, M. Zarei, C. R. Chim. 17, 1264 (2014)

    Article  CAS  Google Scholar 

  54. N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharram, A. Davoodnia, M. Ghassemzadeh, J. Mol. Liq. 163, 122 (2011)

    Article  CAS  Google Scholar 

  55. Z.N. Siddiqui, K. Khan, ACS Sustain. Chem. Eng. 2, 1187 (2014)

    Article  CAS  Google Scholar 

  56. R. Rezaei, F. Moezzi, M.M. Doroodmand, Chin. Chem. Lett. 25, 183 (2014)

    Article  CAS  Google Scholar 

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Acknowledgements

Authors SKP and MMV under UGC-BSR Meritorious Students fellowship and SCB under RGNF are grateful to the University Grants Commission (UGC), India, for financial support and DST-FIST, New Delhi, India, for instrument facilities at the Department of Chemistry, Shivaji University, Kolhapur.

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Authors and Affiliations

  1. Analytical Chemistry and Material Science Research Laboratory, Department of Chemistry, Shivaji University, Kolhapur, Maharashtra, 416004, India

    Sandip K. Patil, Deepak V. Awale, Madagonda M. Vadiyar, Suryakant A. Patil, Sagar C. Bhise & Sanjay S. Kolekar

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  1. Sandip K. Patil
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  2. Deepak V. Awale
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  3. Madagonda M. Vadiyar
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  4. Suryakant A. Patil
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  6. Sanjay S. Kolekar
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Correspondence to Sanjay S. Kolekar.

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Patil, S.K., Awale, D.V., Vadiyar, M.M. et al. Simple protic ionic liquid [Et3NH][HSO4] as a proficient catalyst for facile synthesis of biscoumarins. Res Chem Intermed 43, 5365–5376 (2017). https://doi.org/10.1007/s11164-017-2932-5

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