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A novel straightforward synthesis of α-aminophosphonates: one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a catalyst

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Abstract

We report here a novel and straightforward synthesis method for the preparation of α-aminophosphonates in relatively good yield. The method involves the one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a recyclable catalyst. CuO@Fe3O4 nanoparticles were prepared and their structures were confirmed by the FT-IR, TGA, VSM, TEM and X-ray diffraction patterns analyses.

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References

  1. S. Demkowicz, J. Rachon, M. Daśko, W. Kozak, RSC. Adv. 6, 7101–7112 (2016)

    Article  CAS  Google Scholar 

  2. B. Kaboudin, S. Emadi, A. Hadizadeh, Bioorg. Chem. 37, 101–105 (2009)

    Article  CAS  Google Scholar 

  3. R.L. Hilderbrand, The Role of Phosphonates in Living Systems (CRC Press, Boca Raton, 1982)

    Google Scholar 

  4. D. Redmore, in Topics in Phosphorus Chemistry, vol. 8, ed. by E.J. Griffith, M. Grayson (Wiley, New York, 1976)

    Google Scholar 

  5. B. Kaboudin, M. Karimi, Bioorg. Med. Chem. Lett. 16, 5324–5326 (2006)

    Article  CAS  Google Scholar 

  6. K. Afarinkia, C.W. Rees, Tetrahedron 46, 7175–7196 (1990)

    Article  CAS  Google Scholar 

  7. K. Moonen, I. Laureyn, C.V. Stevens, Chem. Rev. 104, 6177–6215 (2004)

    Article  CAS  Google Scholar 

  8. J.-L. Montchamp, J. Organomet. Chem. 690, 2388–2406 (2005)

    Article  CAS  Google Scholar 

  9. A. Mucha, P. Kafarski, L. Berlicki, J. Med. Chem. 54, 5955–5980 (2011)

    Article  CAS  Google Scholar 

  10. B. Kaboudin, S. Emadi, M.R. Faghihi, M. Fallahi, V.J. Sheikh-Hasani, Enzyme. Inhib. Med. Chem. 28, 576–582 (2013)

    Article  CAS  Google Scholar 

  11. B. Kaboudin, M. Arefi, S. Emadi, V.J. Sheikh-Hasani, Bioorg. Chem. 41–42, 22–27 (2012)

    Article  Google Scholar 

  12. F. Bahrami, F. Panahi, F. Daneshgar, R. Yousefi, M.B. Shahsavani, A. Khalafi-Nezhad, RSC Adv. 6, 5915–5924 (2016)

    Article  CAS  Google Scholar 

  13. K. Devarayan, Y. Sathishkumar, Y.S. Le, B.-S. Kim, PLoS ONE 10, e0139303 (2015)

    Article  Google Scholar 

  14. J. Lewkowski, M.R. Moya, A. Wrona-Piotrowicz, J. Zakrzewski, R. Kontek, G. Gajek, Beilstein J. Org. Chem. 12, 1229–1235 (2016)

    Article  CAS  Google Scholar 

  15. L. Berlicki, M. Bochno, A. Grabowiecka, A. Bialas, P. Kosikowska, P. Kafarski, Amino Acids 42, 1937–1945 (2012)

    Article  CAS  Google Scholar 

  16. B. Palecz, A. Grala, Z. Kudzin, J. Chem. Eng. Data 57, 1515–1519 (2012)

    Article  CAS  Google Scholar 

  17. B. Kaboudin, M. Sorbiun, Tetrahedron Lett. 48, 9015 (2007)

    Article  CAS  Google Scholar 

  18. Kabachnik, M. I.; Medved, T. Ya. Dokl. Akad. Nauk SSSR 1952, 83, 689; Chem. Abstr. 1953, 47, 2724

  19. E. Fields, J. Am. Chem. Soc. 74, 1528 (1952)

    Article  CAS  Google Scholar 

  20. V.P. Kukhar, H.R. Hudson (eds.), Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity (Wiley, Chichester, 2000)

    Google Scholar 

  21. N.S. Zefirov, E.D. Matveeva, Arkivoc 1, 1–17 (2008)

    Google Scholar 

  22. B. Kaboudin, T. Haruki, T. Yamaghishi, T. Yokomatsu, Tetrahedron 63, 8199–8205 (2007)

    Article  CAS  Google Scholar 

  23. K. Moonen, E. Van Meenen, A. Verwee, C.V. Stevens, Angew. Chem. Int. Ed. 44, 7407–7411 (2005)

    Article  CAS  Google Scholar 

  24. A.J. Amali, R.K. Rana, Green Chem. 11, 1781–1786 (2009)

    Article  CAS  Google Scholar 

  25. J. Hu, Y. Wang, M. Han, Y. Zhou, X. Jiang, P. Sun, Catal. Sci. Technol. 2, 2332–2340 (2012)

    Article  CAS  Google Scholar 

  26. Q. Zhang, H. Su, J. Luo, Y. Wei, Catal. Sci. Technol. 3, 235–243 (2013)

    Article  Google Scholar 

  27. B. Kaboudin, Y. Abedi, T. Yokomatsu, Eur. J. Org. Chem. 2011, 6656–6662 (2011)

    Article  CAS  Google Scholar 

  28. B. Kaboudin, Y. Abedi, T. Yokomatsu, Org. Biomol. Chem. 10, 4543–4548 (2012)

    Article  CAS  Google Scholar 

  29. B. Kaboudin, R. Mostafalu, T. Yokomatsu, Green Chem. 15, 2266–2274 (2013)

    Article  CAS  Google Scholar 

  30. R. Mostafalu, B. Kaboudin, F. Kazemi, T. Yokomatsu, RSC Adv. 4, 49273–49279 (2014)

    Article  CAS  Google Scholar 

  31. H. Salemi, B. Kaboudin, F. Kazemi, T. Yokomatsu, RSC Adv. 6, 52656–52664 (2016)

    Article  CAS  Google Scholar 

  32. B. Karimi, A. Zamani, S. Abedi, J.H. Clark, Green Chem. 11, 109–119 (2009)

    Article  CAS  Google Scholar 

  33. B. Karimi, H. Mansouri, H. Vali, Green Chem. 16, 2587–2596 (2014)

    Article  CAS  Google Scholar 

  34. B. Karimi, E. Farhangi, H. Vali, S. Vahdati, ChemSusChem 7, 2735–2741 (2014)

    Article  CAS  Google Scholar 

  35. S.D. McCann, S.S. Stahl, Acc. Chem. Res. 48, 1756–1766 (2015)

    Article  CAS  Google Scholar 

  36. G. Sun, R.E.J. Zhou, J. Sun, H. Ren, RSC Adv. 5, 57058–57066 (2015)

    Article  CAS  Google Scholar 

  37. M.J. Aliaga, D.J. Ramon, M. Yus, Org. Biomol. Chem. 8, 43–46 (2010)

    Article  CAS  Google Scholar 

  38. J.M. Perez, R. Cano, M. Yus, D.J. Ramon, Eur. J. Org. Chem. 2012, 4548–4554 (2012)

    Article  CAS  Google Scholar 

  39. B. Kaboudin, F. Kazemi, F. Habibi, Tetrahedron Lett. 56, 6364–6367 (2015)

    Article  CAS  Google Scholar 

  40. B. Kaboudin, F. Kazemi, F. Habibi, J. Iran. Chem. Soc. 12, 469–475 (2015)

    Article  CAS  Google Scholar 

  41. M.-H. Liao, D.-H. Chen, J. Mater. Chem. 12, 3654–3659 (2002)

    Article  CAS  Google Scholar 

  42. R. Poreddy, C. Enqelbrekt, A. Riisager, Catal. Sci. Technol. 5, 2467–2477 (2015)

    Article  CAS  Google Scholar 

  43. A. Abad, A. Croma, H. Garcia, Chem. Eur. J. 14, 212 (2008)

    Article  CAS  Google Scholar 

  44. P. Fristrup, L.B. Johansen, C.H. Christensen, Catal. Lett. 120, 184 (2008)

    Article  CAS  Google Scholar 

  45. C. Qian, T. Huang, J. Org. Chem. 63, 4125 (1998)

    Article  CAS  Google Scholar 

  46. S.J. Yadav, S.V. Reddy, R. Sreedhar, Green Chem. 4, 436 (2002)

    Article  CAS  Google Scholar 

  47. P.B. Thorat, S.V. Goswami, R.L. Magar, B.R. Patil, S.R. Bhusare, J. Eur, Org. Chem. 2013, 5509–5516 (2013)

    Article  CAS  Google Scholar 

  48. A. Jafari, S. Amini, F. Tamaddon, J. Iran. Chem. Soc. 10, 677–684 (2013)

    Article  CAS  Google Scholar 

  49. M.J. Bhanushali, N.S. Nandurkar, S.R. Jagtap, B.M. Bhanage, Synthetic Commun. 39, 845–859 (2009)

    Article  CAS  Google Scholar 

  50. J. Wu, W. Sun, X. Sun, H.-G. Xia, Green Chem. 8, 365–367 (2006)

    Article  CAS  Google Scholar 

  51. W. Hongjun, D. Tao, C. Chun, J. Fluorine Chem. 168, 144–150 (2014)

    Article  Google Scholar 

  52. R. Gallardo-Macias, K. Nakayama, Synthesis 2010, 57–62 (2010)

    Article  Google Scholar 

  53. K.K. Boroujeni, E.R. Shirazi, M.M. Doroodmand, Phosphorus, Sulfur, Silicon. Rel. Elements 191, 683–688 (2016)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge support by the Institute for Advanced Studies in Basic Sciences (IASBS) Research Council (G2016IASBS31101).

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Correspondence to Babak Kaboudin.

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Kaboudin, B., Kazemi, F. & Hosseini, N.K. A novel straightforward synthesis of α-aminophosphonates: one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a catalyst. Res Chem Intermed 43, 4475–4486 (2017). https://doi.org/10.1007/s11164-017-2890-y

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