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Efficient synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines catalyzed by CuFe2O4 nanoparticles

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Abstract

A simple and efficient method has been developed for the synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines in the presence of CuFe2O4 nanoparticles as a heterogeneous recyclable catalyst at room temperature in high yields.

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References

  1. B.M. Teresa, J.C.M. Adilia, C.D. Maycockd, T. Michaud, Tetrahedron 61, 7960–7966 (2005)

    Article  Google Scholar 

  2. E.J. Corey, F. Zhang, Angew. Chem. Int. Ed. Engl. 38, 1931–1934 (1999)

    Article  CAS  Google Scholar 

  3. C.W. Johannes, M.S. Visser, G.S. Weatherhead, A.H. Hoveyda, J. Am. Chem. 120, 8340–8347 (1998)

    Article  CAS  Google Scholar 

  4. P. O’Brien, Angew. Chem. Int. Ed. Engl. 38, 326–329 (1999)

    Article  Google Scholar 

  5. G. Li, H.T. Chang, K.B. Sharpless, Angew. Chem. Int. Ed. Engl. 35, 451–454 (1996)

    Article  CAS  Google Scholar 

  6. D.J. Ager, I. Prakash, S.R. Schaad, Chem. Rev. 96, 835–876 (1996)

    Article  CAS  Google Scholar 

  7. G. Huerta, G.C. Ordonez, C. Alvarez-Toledano, V. Santes, E. Gomez, R.A. Toscano, Synth. Commun. 34, 2393–2406 (2004)

    Article  CAS  Google Scholar 

  8. S.W. Wei, K.A. Stingl, K.M. Weiss, S.B. Tsogoeva, Synlett 5, 707–711 (2010)

    Google Scholar 

  9. D.M. Hodgson, A.R. Gibbs, G.P. Lee, Tetrahedron 52, 14361–14384 (1996)

    Article  CAS  Google Scholar 

  10. R.M. Hanson, Chem. Rev. 91, 437–475 (1991)

    Article  CAS  Google Scholar 

  11. A.S. Rao, S.K. Paknikar, J.G. Kirtane, Tetrahedron 39, 2323–2367 (1983)

    Article  CAS  Google Scholar 

  12. J.A. Deyrup, C.L. Moyer, J. Org. Chem. 34, 175–179 (1969)

    Article  CAS  Google Scholar 

  13. P.A. Crooks, R. Szyudler, Chem. Ind., 1111–1112 (1973)

  14. H. Eshghi, M. Rahimizadeh, A. Shoryabi, J. Iran. Chem. Soc. 2, 155–160 (2005)

    Article  CAS  Google Scholar 

  15. M. Hosseini-Sarvari, H. Sharghi, J. Iran. Chem. Soc. 5, 384–393 (2008)

    Article  CAS  Google Scholar 

  16. D.B.G. Williams, M. Lawton, Tetrahedron Lett. 47, 6557–6560 (2006)

    Article  CAS  Google Scholar 

  17. A. Procopio, M. Gaspari, M. Nardi, M. Oliverio, O. Rosati, Tetrahedron Lett. 49, 2289–2293 (2008)

    Article  CAS  Google Scholar 

  18. L.R. Reddy, M.A. Reddy, N. Bhanumathi, K.R. Rao, New J. Chem. 25, 221–222 (2001)

    Article  CAS  Google Scholar 

  19. T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 43, 7891–7893 (2002)

    Article  CAS  Google Scholar 

  20. M.C. Singh, R.K. Peddinti, Tetrahedron Lett. 48, 7354–7357 (2007)

    Article  CAS  Google Scholar 

  21. A.K. Chakraborti, A. Kondaskar, Tetrahedron Lett. 44, 8315–8319 (2003)

    Article  CAS  Google Scholar 

  22. J.R. Rodriguez, A. Navarro, Tetrahedron Lett. 45, 7495–7498 (2004)

    Article  CAS  Google Scholar 

  23. G. Sundararajan, K. Vijayakrishna, B. Varghese, Tetrahedron Lett. 45, 8253–8256 (2004)

    Article  CAS  Google Scholar 

  24. A. Kamal, R.R. Ramu, M.A. Azhar, G.B.R. Khanna, Tetrahedron Lett. 46, 2675–2677 (2005)

    Article  CAS  Google Scholar 

  25. M. Maheswara, K.S.V.K. Rao, J.Y. Do, Tetrahedron Lett. 49, 1795–1800 (2008)

    Article  CAS  Google Scholar 

  26. J.S. Yadav, B.V.S. Reddy, A.K. Basak, A.V. Narasaiah, Tetrahedron Lett. 44, 1047–1050 (2003)

    Article  CAS  Google Scholar 

  27. H. Kotsuki, T. Shimanouchi, M. Teraguchi, M. Kataoka, A. Tatsukawa, H. Nishizawa, Chem. Lett., 2159–2162 (1994)

  28. A.K. Chakraborti, S. Rudrawar, A. Kondaskar, Org. Biomol. Chem. 2, 1277–1280 (2004)

    Article  CAS  Google Scholar 

  29. B.M. Reddy, K.M. Patil, B.T. Reddy, S.E. Park, Catal. Commun. 9, 950–954 (2008)

    Article  CAS  Google Scholar 

  30. M.J. Bhanushali, N.S. Nandurkar, M.D. Bhor, B.M. Bhanage, Tetrahedron Lett. 49, 3672–3676 (2008)

    Article  CAS  Google Scholar 

  31. S. Chikazumi, S. Taketomi, M. Ukita, M. Mizukami, H. Miyajima, M. Setogawa, Y. Kurihara, J. Magn. Magn. Mater. 65, 245–251 (1987)

    Article  CAS  Google Scholar 

  32. A.H. Lu, W. Schmidt, N. Matoussevitch, H. Pnnermann, B. Spliethoff, B. Tesche, E. Bill, W. Kiefer, F. Schüth, Angew. Chem. 116, 4403–4410 (2004)

    Article  Google Scholar 

  33. S.C. Tsang, V. Caps, I. Paraskevas, D. Chadwick, D. Thompsett, Angew. Chem. 116, 5763–5767 (2004)

    Article  Google Scholar 

  34. T. Hyeon, Chem. Commun., 927–934 (2003)

  35. D.W. Elliott, W.X. Zhang, Environ. Sci. Technol. 35, 4922–4926 (2001)

    Article  CAS  Google Scholar 

  36. M. Takafuji, S. Ide, H. Ihara, Z. Xu, Chem. Mater. 16, 1977–1983 (2004)

    Article  CAS  Google Scholar 

  37. I. Nedkov, R.E. Vandenberghe, T. Marinova, Ph. Thailhades, T. Merodiiska, I. Avramova, Magnetic CuFe2O4 nanoparticles were prepared according to literature. Appl. Surf. Sci. 253, 2589–2596 (2006)

    Article  CAS  Google Scholar 

  38. I. Cepanec, M. Litvic, H. Mikuldas, A. Bartolinčić, V. Vinković, Tetrahedron 59, 2435–2439 (2003)

    Article  CAS  Google Scholar 

  39. H. Danafar, B. Yadollahi, Catal. Commun. 10, 842–847 (2009)

    Article  CAS  Google Scholar 

  40. A.T. Placzek, J.L. Donelson, R. Trivedi, R.A. Gibbs, S.K. De, Tetrahedron Lett. 46, 9029–9034 (2005)

    Article  CAS  Google Scholar 

  41. N. Azizi, M.R. Saidi, Org. Lett. 7, 3649–3651 (2005)

    Article  CAS  Google Scholar 

  42. M.M. Mojtahedi, M.S. Abaee, V. Hamidi, Catal. Commun. 8, 1671–1674 (2007)

    Article  CAS  Google Scholar 

  43. A.T. Placzek, J.L. Donelson, R. Trivedi, A.R. Gibbs, S.K. De, Tetrahedron Lett. 46, 9029–9034 (2005)

    Article  CAS  Google Scholar 

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Acknowledgments

We would like to thank the Islamic Azad University; Ayatollah Amoli Branch for generous financial support of the research project.

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Correspondence to Seyed Meysam Baghbanian.

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Baghbanian, S.M., Farhang, M. Efficient synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines catalyzed by CuFe2O4 nanoparticles. J IRAN CHEM SOC 10, 1033–1037 (2013). https://doi.org/10.1007/s13738-013-0241-5

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  • DOI: https://doi.org/10.1007/s13738-013-0241-5

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