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A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones

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Abstract

A novel dicationic ionic liquid, N,N,N′,N′-tetramethyl-N,N′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs]2), has been produced, and identified by analysis of its 1H NMR, 13C NMR, FT-IR, mass and thermal gravimetric data. Thereafter, it has been utilized as a highly effectual, homogeneous and dual-functional catalyst to promote the multi-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride and arylaldehydes under solvent-free conditions for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones. Due to the dual-functionality of [TMBSED][OMs]2 (possessing acidic and basic sites), and also having two sites of each, it was a highly effective and general catalyst for the synthesis. Moreover, a plausible and attractive mechanism based on the dual-functionality of the catalyst has been proposed.

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References

  1. P. Diana, A. Carbone, P. Barraja, G. Kelter, H.-H. Fiebig, G. Cirrincione, Bioorg. Med. Chem. 18, 4524 (2010)

    Article  CAS  PubMed  Google Scholar 

  2. M.M.M. Santos, N. Faria, J. Iley, S.J. Coles, M.B. Hursthouse, M.L. Martins, R. Moreira, Bioorg. Med. Chem. Lett. 20, 193 (2010)

    Article  PubMed  CAS  Google Scholar 

  3. H. Kan, I. Adachi, R. Kido, K. Hirose, J. Med. Chem. 10, 411 (1967)

    Article  Google Scholar 

  4. Y.Y. Kang, K.J. Shin, K.H. Yo, K.J. Seo, C.Y. Hong, C.S. Lee, S.Y. Park, D.J. Kim, S.W. Park, Bioorg. Med. Chem. Lett. 10, 95 (2000)

    Article  CAS  PubMed  Google Scholar 

  5. A. Padmaja, C. Rajasekhar, A. Muralikrishna, V. Padmavathi, Eur. J. Med. Chem. 46, 5034 (2011)

    Article  CAS  PubMed  Google Scholar 

  6. B.-L. Deng, M.D. Cullen, Z. Zhou, T.L. Hartman, R.W.J. Buckheit, C. Pannecouque, E.D. Clercq, P.E. Fanwick, M. Cushman, Bioorg. Med. Chem. 14, 2366 (2006)

    Article  CAS  PubMed  Google Scholar 

  7. J.J. Talley, D.L. Brown, J.S. Carter, M.J. Graneto, C.M. Koboldt, J.L. Masferrer, W.E. Perkins, R.S. Rogers, A.F. Shaffer, Y.Y. Zhang, B.S. Zweifel, K. Seibert, J. Med. Chem. 43, 775 (2000)

    Article  CAS  PubMed  Google Scholar 

  8. X.H. Zhang, Y.H. Zhan, D. Chen, F. Wang, L.Y. Wang, Dyes Pigm. 93, 1408 (2012)

    Article  CAS  Google Scholar 

  9. Z. Yang, K. Zhang, F. Gong, S. Li, J. Chen, J.S. Ma, L.N. Sobenia, A.I. Mikhaleva, G. Yang, B.A. Trofirmov, Beilstein J. Org. Chem. 7, 46 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. T. Ishioka, A. Kubo, Y. Koiso, K. Nagasawa, A. Itai, Y. Hashimoto, Bioorg. Med. Chem. 10, 1555 (2002)

    Article  CAS  PubMed  Google Scholar 

  11. F. Saikh, J. Das, S. Ghosh, Tetrahedron Lett. 54, 4679 (2013)

    Article  CAS  Google Scholar 

  12. M. Mashhadinezhad, F. Shirini, M. Mamaghani, Microporous Mesoporous Mater. 262, 269 (2018)

    Article  CAS  Google Scholar 

  13. M.G. Dekamin, S.Z. Peyman, Monatsh. Chem. 147, 445 (2016)

    Article  CAS  Google Scholar 

  14. A.U. Khandebharad, S.R. Sarda, C.H. Gill, B.R. Agrawal, Res. J. Chem. Sci. 5, 27 (2015)

    CAS  Google Scholar 

  15. H. Kiyani, H. Darbandi, A. Mosallanezhad, F. Ghorbani, Res. Chem. Intermed. 41, 7561 (2015)

    Article  CAS  Google Scholar 

  16. H. Kiyani, F. Ghorbani, A. Kanaani, D. Ajloo, M. Vakilim, Res. Chem. Intermed. 41, 7739 (2015)

    Article  CAS  Google Scholar 

  17. M.S. Patil, C. Mudaliar, G.U. Chaturbhuj, Tetrahedron Lett. 58, 3256 (2017)

    Article  CAS  Google Scholar 

  18. S.N. Maddila, S. Maddila, W.E. van Zyl, S.B. Jonnalagadda, Res. Chem. Intermed. 42, 2553 (2016)

    Article  CAS  Google Scholar 

  19. A. Rikani, D. Setamdideh, Orient. J. Chem. 32, 1433 (2016)

    Article  CAS  Google Scholar 

  20. J. Safari, M. Ahmadzadeh, Z. Zarnegar, Catal. Commun. 86, 91 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  22. F. Tamaddon, D. Azadi, J. Mol. Liq. 255, 406 (2018)

    Article  CAS  Google Scholar 

  23. S. Ahmadi, A. Zare, M. Aali-Hosaini, M. Maghsoudi, S. Izadpanah, A. Parhami, M. Merajoddin, Res. Chem. Intermed. 42, 6245 (2016)

    Article  CAS  Google Scholar 

  24. A. Zare, E. Sharif, A. Arghoon, M. Ghasemi, B. Dehghani, S. Ahmad-Zadeh, F. Zarei, Iran. J. Catal. 7, 233 (2017)

    Google Scholar 

  25. A.S. Khan, Z. Man, M.A. Bustam, C.F. Kait, A. Nasrullah, Z. Ullah, A. Sarwono, P. Ahamd, N. Muhammad, J. Clean. Prod. 170, 591 (2018)

    Article  CAS  Google Scholar 

  26. A. Sarwono, Z. Man, N. Muhammad, A.S. Khan, W.S.W. Hamzah, A.H. Abdul Rahim, Z. Ullah, C.D. Wilfred, Ultrason. Sonochem. 37, 310 (2017)

    Article  CAS  PubMed  Google Scholar 

  27. A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A Gen. 467, 61 (2013)

    Article  CAS  Google Scholar 

  28. E.C. Lopes Pereira, J.M.F. da Silva, R.B. Jesus, B.G. Soares, S. Livi, Eur. Polym. J. 97, 104 (2017)

    Article  CAS  Google Scholar 

  29. M. Akrami Abarghooei, R. Mohebat, Z. Karimi-Jaberi, M.H. Mosslemin, Catal. Commun. 105, 59 (2018)

    Article  CAS  Google Scholar 

  30. P. Kour, V.P. Singh, B. Khajuria, T. Singh, A. Kumar, Tetrahedron Lett. 58, 4179 (2017)

    Article  CAS  Google Scholar 

  31. A. Khalafi-Nezhad, M. Shekouhy, H. Sharghi, J. Aboonajmi, A. Zare, RSC Adv. 6, 67281 (2016)

    Article  CAS  Google Scholar 

  32. S. Traboni, F. Liccardo, E. Bedini, M. Giordano, A. Iadonisi, Tetrahedron Lett. 58, 1762 (2017)

    Article  CAS  Google Scholar 

  33. A. Zare, M. Merajoddin, A.R. Moosavi-Zare, M. Zarei, M.H. Beyzavi, M.A. Zolfigol, Res. Chem. Intermed. 42, 2365 (2016)

    Article  CAS  Google Scholar 

  34. M. Shekouhy, A. Moaddeli, A. Khalafi-Nezhad, J. Ind. Eng. Chem. 50, 41 (2017)

    Article  CAS  Google Scholar 

  35. A. Zare, M. Dashtizadeh, M. Merajoddin, Iran. Chem. Commun. 3, 208 (2015)

    CAS  Google Scholar 

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Acknowledgement

We thank the Research Council of Payame Noor University for providing the necessary research facilities and the financial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

    Navid Irannejad-Gheshlaghchaei, Abdolkarim Zare, Seyed Sajad Sajadikhah & Alireza Banaei

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  1. Navid Irannejad-Gheshlaghchaei
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  2. Abdolkarim Zare
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  3. Seyed Sajad Sajadikhah
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  4. Alireza Banaei
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Correspondence to Abdolkarim Zare or Seyed Sajad Sajadikhah.

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Irannejad-Gheshlaghchaei, N., Zare, A., Sajadikhah, S.S. et al. A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones. Res Chem Intermed 44, 6253–6266 (2018). https://doi.org/10.1007/s11164-018-3488-8

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