Skip to main content
Log in

One-Pot Synthesis of 1-Aminophosphinic acids using 50% Hypophosphorus Acid under microwave irradiation

  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A simple and efficient method has been developed for the synthesis of α-aminophosphinic acids from hypophosphorus acid under solvent-free conditions using microwave irradiation. α-Aminophosphinic acids were obtained in high yield under mild conditions by reaction of hypophosphorus acid with aldehydes in the presence of amines under microwave irradiation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R. Engel, Chem. Rev. 77 (1977) 349

    CAS  Google Scholar 

  2. K. Moonen, I. Laureyn and C.V. Stevens, Chem. Rev. 104 (2004) 6177.

    CAS  Google Scholar 

  3. J.G. Dingwall, C.D. Campell and E.K. Baylis, UK Pat. Appl., 1 (1979) 542 938.

    Google Scholar 

  4. P. Kafarski, B. Lejczak, R. Tyka, L. Koba, E. Pliszczak & P. Wieczorek, J. Plant Growth Regulation 14 (1995) 199.

    CAS  Google Scholar 

  5. Y. Ishiguri, Y. Yamada, T. Kato, M. Sasaki and K. Mukai, Eur. Pat. Appl., EP 82 (1982) 301905

    Google Scholar 

  6. R. Gancarz, S. Chakraborty, Synthesis (1977) 625

    Google Scholar 

  7. P.P. Giannousis, P.A. Bartlett, J. Med. Chem. 30 (1987) 1603

    CAS  Google Scholar 

  8. L. Maier, P.J. Lea, Phosphorus, Sulfur, and Silicon 17 (1983) 1

    CAS  Google Scholar 

  9. R.L. Hilderbrand, The Role of Phosphonates in Living Systems, CRC Press: Boca Raton, F1 (1982)

    Google Scholar 

  10. P. Kafarski, B. Lejczak, Phosphorus, Sulfur, and Silicon 63 (1991) 193

    CAS  Google Scholar 

  11. V.P. Kukhar, H.R. Hudson, Aminophosphonic and Aminophosphinic Acids, John Wiley & Sons, (2000)

    Google Scholar 

  12. S. Hanessian, Y.L. Bennani, Synthesis (1995) 1272.

    Google Scholar 

  13. D. Redmore, Topics in Phosphorus Chemistry, Griffith, E. J.; Grayson, M. Eds.; Vol. 8; Wiley: New York, (1976)

    Google Scholar 

  14. F.R. Atherton, C.H. Hassall and R.W. Lambert, J. Med. Chem. 29 (1986) 29

    CAS  Google Scholar 

  15. M.C. Allen, W. Fuhrer, B. Tuck, R. Wade and J.M. Wood, J. Med. Chem. 32 (1989) 1652

    CAS  Google Scholar 

  16. C.H. Hassall, Antibiotics, ed. F. E. Hahn, Springer Verlag, Berlin, Vol VI (1983) 1

    Google Scholar 

  17. R. Gancarz, J.S. Wieczorek, Synthesis (1978) 625

    Google Scholar 

  18. D. Seyferth, R.S. Marmor, P. Hilbert, J. Org. Chem. 36 (1971) 1379

    Google Scholar 

  19. K.H. Worms, M. Schmidt-Dunker, Organic Phosphorus Compounds, G.M. Kosolapoff, L. Marier, Eds., John Wiley & Sons, New York, Vol. 7 (1976) 1

    Google Scholar 

  20. B. Kaboudin, Phosphorus, Sulfur and Silicon 177 (2002) 1749

    CAS  Google Scholar 

  21. S. Bhagat, A.K. Chakraborti, J. Org. Chem. 72 (2007) 1263.

    CAS  Google Scholar 

  22. J. Barycki, P. Mastalerz and M. Soroka, Tetrahedron Lett. 36 (1970) 3147.

    Google Scholar 

  23. J.P. Genet, J. Uziel, M. Port, A.M. Touzin, S. Roland, S. Thorimbert and S. Tanier, Tetrahedron Lett. 33 (1992) 77

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  25. B.C. Ranu, A. Hajira and U. Jana, Org. Lett. 1 (1999) 1141

    CAS  Google Scholar 

  26. K. Manabe, S. Kobayashi, Chem. Commun. (2000) 669

    Google Scholar 

  27. S. Chandrasekhar, S.J. Prakash, V. Jagadeshwar and C. Narsihmulu, Tetrahedron Lett. 42 (2001) 5561

    CAS  Google Scholar 

  28. H. Firouzabadi, N. Iranpoor & S. Sobhani, Synthesis (2004) 2692

    Google Scholar 

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

    CAS  Google Scholar 

  30. B. Kaboudin, E. Jafari, Synthesis (2007) 1823.

    Google Scholar 

  31. H. Schmidt, Chem. Ber. 81 (1948) 477

    CAS  Google Scholar 

  32. W.M. Linfield, E. Jungermann and A.T. Guttmann, J. Org. Chem. 26 (1961) 4088

    CAS  Google Scholar 

  33. T. Yamagishi, T. Haruki and T. Yokomatsu, Tetrahedron 62 (2006) 9210

    CAS  Google Scholar 

  34. L.A. Cates, V.S. Li, Pharm. Res. (1985) 136

    Google Scholar 

  35. A. Lecoq, A. Yiotakis and V. Dive, Synth. Commun. 24 (1994) 2877

    CAS  Google Scholar 

  36. R. Hamilton, B. Walker and B.J. Walker, Tetrahedron Lett. 36 (1995) 4451

    CAS  Google Scholar 

  37. B. Kaboudin, N. As-Habei, Tetrahedron Lett. 44 (2003) 4243

    CAS  Google Scholar 

  38. J.-L. Pirat, J. Monbrun, D. Virieux, J.-N. Volle, M. Tillard and M.H.-J. Cristau, J. Org. Chem. 70 (2005) 7035

    CAS  Google Scholar 

  39. E.A. Boyd, W.C. Chan and V.M.Jr. Loh, Tetrahedron Lett. 37 (1996) 1647

    CAS  Google Scholar 

  40. X.-Y. Jiao, C. Verbruggen, M. Borloo, W. Bollaert, A.D. Groot, R. Dommisse and A. Haemers, Synthesis (1994) 23.

    Google Scholar 

  41. J. Lewkowski, J. Organometallic Chem. 681 (2003) 225

    CAS  Google Scholar 

  42. J. Lewkowski, Heteroat. Chem. 15 (2004) 162.

    CAS  Google Scholar 

  43. B. Kaboudin, R. Nazari, Synth. Commun. 31 (2001) 2245

    CAS  Google Scholar 

  44. B. Kaboudin, M.S. Balakrishna, Synth. Commun. 31 (2001) 2773

    CAS  Google Scholar 

  45. B. Kaboudin, Tetrahedron Lett. 43 (2002) 8713

    CAS  Google Scholar 

  46. B. Kaboudin, Tetrahedron Lett. 44 (2003) 1051

    CAS  Google Scholar 

  47. B. Kaboudin, A. Rahmani, Synthesis (2003) 2705

    Google Scholar 

  48. B. Kaboudin, F. Saadati, Synthesis (2004) 1249

    Google Scholar 

  49. B. Kaboudin, A. Rahmani, Org. Prep. Proced. Int. 36 (2004) 82

    CAS  Google Scholar 

  50. B. Kaboudin, H. Haghighat, Tetrahedron Lett. 46 (2005) 7955

    CAS  Google Scholar 

  51. B. Kaboudin, H. Haghighat and T. Yokomatsu, J. Org. Chem. 71 (2006) 6604.

    CAS  Google Scholar 

  52. S. Caddick, Tetrahedron 51 (1995) 10403

    CAS  Google Scholar 

  53. A. Zlotorzynsky, Crit. Rev. Anal. Chem. 25 (1995) 43

    Google Scholar 

  54. R.S. Varma, Green Chem. (1999) 43

    Google Scholar 

  55. P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron 57 (2001) 9225

    CAS  Google Scholar 

  56. L. Perreux, A. Loupy, Tetrahedron 57 (2001) 9199

    CAS  Google Scholar 

  57. B. Kaboudin, Chem. Lett. (2001) 880

    Google Scholar 

  58. B. Kaboudin, R. Nazari, Tetrahedron Lett. 42 (2001) 8211

    CAS  Google Scholar 

  59. M.S. Balakrishna, B. Kaboudin, Tetrahedron Lett. 42 (2001) 1127

    CAS  Google Scholar 

  60. B. Kaboudin, K. Navaee, Heterocycles 55 (2001) 1443

    CAS  Google Scholar 

  61. B. Kaboudin, K. Navaee, Heterocycles 60 (2003) 2287

    CAS  Google Scholar 

  62. B. Kaboudin, F. Saadati, J. Heterocycl. Chem. 42 (2005) 699

    CAS  Google Scholar 

  63. B. Kaboudin, F. Saadati, Heterocycles 65 (2005) 353

    CAS  Google Scholar 

  64. A. Loupy, Microwaves in Organic Synthesis (2nd reprint), Wiley- VCH, Weinheim (2004).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to B. Kaboudin.

Additional information

Dedicated to Professor Habib Firouzabadi on the occasion of his 65 birthday and also his retirement

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kaboudin, B., Jafari, E. One-Pot Synthesis of 1-Aminophosphinic acids using 50% Hypophosphorus Acid under microwave irradiation. JICS 5 (Suppl 1), S97–S102 (2008). https://doi.org/10.1007/BF03246496

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03246496

Keywords

Navigation