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Application of copper iodide nanoparticles immobolized porous polysulfonamide gel as an effective nanocatalyst for synthesis of aminoindolizines

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Abstract

In this paper, we investigate the catalytic activity of CuI NPs supported on porous cross-linked poly(ethyleneamine)–polysulfonamide (PEA–PSA@CuI) as an effective and recyclable nanocatalyst for the synthesis of indolizine derivatives. Three-component reaction of 2-pyridine carbaldehyde with phenylacetylene and second-order amines in the presence of PEA–PSA@CuI as catalyst under solvent-free conditions resulted amino indolizine products in good to excellent yields. The present catalytic system offers advantages such as high catalytic activity in short reaction time, recovered the catalyst by centrifugation and recycled for five times without significant loss in its efficiency.

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References

  1. J. Gerencsér, G. Dormán, F. Darvas, QSAR Comb. Sci. 25, 439–448 (2006)

    Google Scholar 

  2. D.J. Ramón, M. Yus, Angew. Chem. Int. Ed. 44, 1602–1634 (2005)

    Google Scholar 

  3. C. Hulme, V. Gore, Curr. Med. Chem. 10, 51–80 (2003)

    CAS  PubMed  Google Scholar 

  4. R.J. Molyneux, L.F. James, Science 216, 190–191 (1982)

    CAS  PubMed  Google Scholar 

  5. L.L. Gundersen, C. Charnock, A.H. Negussie, F. Rise, S. Teklu, Eur. J. Pharm. Sci. 30, 26–35 (2007)

    CAS  PubMed  Google Scholar 

  6. L.L. Gundersen, K.E. Malterud, A.H. Negussie, F. Rise, S. Teklu, O.B. Østby, Bioorg. Med. Chem. 11, 5409–5419 (2003)

    CAS  PubMed  Google Scholar 

  7. V.R. Vemula, S. Vurukonda, C.K. Bairi, Int. J. Pharm. Sci. Rev. Res. 11, 159–163 (2011)

    CAS  Google Scholar 

  8. T. Weide, L. Arve, H. Prinz, H. Waldmann, H. Kessler. Bioorg. Med. Chem. Lett 16, 59–63 (2006)

    CAS  PubMed  Google Scholar 

  9. W.O. Foye, Foye’s Principles of Medicinal Chemistry (Lippincott Williams and Wilkins, 2008)

  10. Y.D.A. James, K. Koya, H. Li, G. Liang, Z. Xia, W. Ying, L. Sun, Bioorg. Med. Chem. Lett. 18, 1784–1787 (2008)

    CAS  PubMed  Google Scholar 

  11. M.W. Edwards, J.W. Daly, C.W. Myers, J. Nat. prod. 51, 1188–1197 (1988)

    CAS  PubMed  Google Scholar 

  12. Y. Hu, J. Ren, L. Wang, X. Zhao, M. Zhang, K. Shimizu, C. Zhang, Phytochemistry 149, 12–23 (2018)

    CAS  PubMed  Google Scholar 

  13. C. Sandeep, K.N. Venugopala, R.M. Gleiser, A. Chetram, B. Padmashali, R.S. Kulkarni, B. Odhav, Chem. Biol. Drug. Des. 88, 899–904 (2016)

    CAS  PubMed  Google Scholar 

  14. N. Ortega, D.T.D Tang, S. Urban, D. Zhao, F. Glorius. Angew. Chem. Int. Ed. 52, 9500–9503 (2013).

    CAS  Google Scholar 

  15. C. Sandeep, B. Padmashali, R.S. Kulkarni, Tetrahedron Lett. 54, 6411–6414 (2013)

    CAS  Google Scholar 

  16. K.M. Elattar, I. Youssef, A.A. Fadda, Synth. Commun. 46, 719–744 (2016)

    CAS  Google Scholar 

  17. S.H. Hedges, R.B. Herbert, E. Knagg, V. Pasupathyt, Tetrahedron lett. 29, 807–810 (1988)

    CAS  Google Scholar 

  18. R.J. Andersen, D.J. Faulkner, C.H. He, G.D. Van Duyne, J. Clardy, J. Am. Chem. Soc. 107, 5492–5495 (1985)

    CAS  Google Scholar 

  19. V. Boekelheide, R.J. Windgassen, J. Am. Chem. Soc. 81, 1456–1459 (1959)

    CAS  Google Scholar 

  20. J. Hurst, T. Melton, D.G. Wibberley, J. Chem. Soc. 529, 2948–2955 (1965)

    Google Scholar 

  21. G. Poissonnet, M.H. Théret-Bettiol, R.H. Dodd, J. Org. Chem. 61, 2273–2282 (1996)

    CAS  Google Scholar 

  22. J. Barluenga, G. Lonzi, L. Riesgo, L.A. Lopez, M.J. Tomas, Am. Chem. Soc. 132, 13200–13202 (2010)

    CAS  Google Scholar 

  23. J.B. Xia, S.L. You, Org. Lett. 11, 1187–1190 (2009)

    CAS  PubMed  Google Scholar 

  24. J. Kaloko, A. Hayford, Org. Lett. 7, 4305–4308 (2005)

    CAS  PubMed  Google Scholar 

  25. P.L. Reddy, R. Arundhathi, M. Tripathi, D.S. Rawat, RSC Adv. 6, 53596–53601 (2016)

    CAS  Google Scholar 

  26. U.C. Rajesh, G. Purohit, D.S. Rawat, ACS. Sus. Chem. Eng. 3, 2397–2404 (2015)

    CAS  Google Scholar 

  27. E. Akhavan Taheri, S. Hemmati, M. Hekmati, H. Veisi, New J. Chem. 42, 14009–14009 (2018)

    CAS  Google Scholar 

  28. H. Veisi, M. Hamelian, S. Hemmati, A. Dalvand, Tetrahedron Lett. 58, 4440–4446 (2017)

    CAS  Google Scholar 

  29. H. Veisi, Y. Metghalchi, M. Hekmati, S. Samadzadeh, Appl. Organomet. Chem. 31, e3676 (2017)

    Google Scholar 

  30. M. Adib, V. Sadeghi, H. Veisi, Tetrahedron lett. 59, 1928–1931 (2018)

    CAS  Google Scholar 

  31. H. Hojat Veisi, S.A. Ahmadian, K. Mirshokraie, M.M. Didehban, Appl Zangeneh, Organomet. Chem. 33, e4737 (2019)

    Google Scholar 

  32. Y. Yang, C. Xie, Y. Xie, Y. Zhang, Org. Lett. 14, 957–959 (2012)

    CAS  PubMed  Google Scholar 

  33. V. Helan, A.V. Gulevich, V. Gevorgyan, Chem. Sci. 6, 1928–1931 (2015)

    CAS  PubMed  PubMed Central  Google Scholar 

  34. S.S. Patil, S.V. Patil, V.D. Bobade, Synlett 2011, 1157–1159 (2011)

    Google Scholar 

  35. B. Sarmah, B. Satpati, R. Srivastava, RSC Adv. 6, 87066–87081 (2016)

    CAS  Google Scholar 

  36. G.H. Dang, H.Q. Lam, A.T. Nguyen, D.T. Le, T. Truong, N.T. Phan, J. Catal. 337, 167–176 (2016)

    CAS  Google Scholar 

  37. M.J. Albaladejo, F. Alonso, M.J. González-Soria, ACS Catalysis. 5, 3446–3456 (2015)

    CAS  Google Scholar 

  38. B. Yan, Y. Liu, Org. Lett. 9, 4323–4326 (2007)

    CAS  PubMed  Google Scholar 

  39. S. Mishra, B. Naskar, R. Ghosh, Tetrahedron Lett. 53, 5483–5487 (2012)

    CAS  Google Scholar 

  40. S. Mishra, A.K. Bagdi, M. Ghosh, S. Sinha, A. Hajra, RSC Adv. 4, 6672–6676 (2014)

    CAS  Google Scholar 

  41. R. Ghorbani-Vaghei, H. Jalili, Synthesis 7, 1099–1102 (2005)

    Google Scholar 

  42. R. Ghorbani-Vaghei, N. Sarmast, Can. J. Chem. 95, 1073–1080 (2017)

    CAS  Google Scholar 

  43. S. Alavinia, R. Ghorbani-Vaghei, J. Rakhtshah, J. Yousefi Seyf, I. Ali Arabian, Appl Organomet Chem. 34(3), e5449 (2020)

    CAS  Google Scholar 

  44. R. Ghorbani-Vaghei, S. Alavinia, N. Sarmast, Appl. Organomet. Chem. 32, e 4038 (2018)

    Google Scholar 

  45. R. Ghorbani-Vaghei, S. Alavinia, Z. Merati, V. Izadkhah, Appl. Organomet. Chem. 32, e 4127 (2018)

    Google Scholar 

  46. A. Kharazmi, R. Ghorbani-Vaghei, S. Alavinia, ChemistrySelect. 5, 1424–1430 (2020)

    CAS  Google Scholar 

  47. A. Fatehi, R. Ghorbani-Vaghei, S. Alavinia, J. Mahmoodi, ChemistrySelect. 5, 944–951 (2020)

    CAS  Google Scholar 

  48. S. Alavinia, R. Ghorbani-Vaghei, New. J. Chem. 44, 13062–13073 (2020)

    CAS  Google Scholar 

  49. S. Alavinia, R. Ghorbani-Vaghei, J. Phys. Chem. Solids. 146, 109573 (2020)

    CAS  Google Scholar 

  50. F. Hamidi Dastjerdi, R. Ghorbani-Vaghei, S. Alavinia, Catal. Lett. (2020). https://doi.org/10.1007/s10562-020-03265-1

    Article  Google Scholar 

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Acknowledgements

The authors wish to thank Bu-Ali Sina University, Center of Excellence Developmental of Environmentally Friendly Methods for Chemical Synthesis (CEDEFMCS) for financial support to carry out this research.

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Correspondence to Ramin Ghorbani-Vaghei.

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Solgi, S., Ghorbani-Vaghei, R. & Alavinia, S. Application of copper iodide nanoparticles immobolized porous polysulfonamide gel as an effective nanocatalyst for synthesis of aminoindolizines. J Porous Mater 28, 289–298 (2021). https://doi.org/10.1007/s10934-020-00989-8

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