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.
Similar content being viewed by others
References
R. Engel, Chem. Rev. 77 (1977) 349
K. Moonen, I. Laureyn and C.V. Stevens, Chem. Rev. 104 (2004) 6177.
J.G. Dingwall, C.D. Campell and E.K. Baylis, UK Pat. Appl., 1 (1979) 542 938.
P. Kafarski, B. Lejczak, R. Tyka, L. Koba, E. Pliszczak & P. Wieczorek, J. Plant Growth Regulation 14 (1995) 199.
Y. Ishiguri, Y. Yamada, T. Kato, M. Sasaki and K. Mukai, Eur. Pat. Appl., EP 82 (1982) 301905
R. Gancarz, S. Chakraborty, Synthesis (1977) 625
P.P. Giannousis, P.A. Bartlett, J. Med. Chem. 30 (1987) 1603
L. Maier, P.J. Lea, Phosphorus, Sulfur, and Silicon 17 (1983) 1
R.L. Hilderbrand, The Role of Phosphonates in Living Systems, CRC Press: Boca Raton, F1 (1982)
P. Kafarski, B. Lejczak, Phosphorus, Sulfur, and Silicon 63 (1991) 193
V.P. Kukhar, H.R. Hudson, Aminophosphonic and Aminophosphinic Acids, John Wiley & Sons, (2000)
S. Hanessian, Y.L. Bennani, Synthesis (1995) 1272.
D. Redmore, Topics in Phosphorus Chemistry, Griffith, E. J.; Grayson, M. Eds.; Vol. 8; Wiley: New York, (1976)
F.R. Atherton, C.H. Hassall and R.W. Lambert, J. Med. Chem. 29 (1986) 29
M.C. Allen, W. Fuhrer, B. Tuck, R. Wade and J.M. Wood, J. Med. Chem. 32 (1989) 1652
C.H. Hassall, Antibiotics, ed. F. E. Hahn, Springer Verlag, Berlin, Vol VI (1983) 1
R. Gancarz, J.S. Wieczorek, Synthesis (1978) 625
D. Seyferth, R.S. Marmor, P. Hilbert, J. Org. Chem. 36 (1971) 1379
K.H. Worms, M. Schmidt-Dunker, Organic Phosphorus Compounds, G.M. Kosolapoff, L. Marier, Eds., John Wiley & Sons, New York, Vol. 7 (1976) 1
B. Kaboudin, Phosphorus, Sulfur and Silicon 177 (2002) 1749
S. Bhagat, A.K. Chakraborti, J. Org. Chem. 72 (2007) 1263.
J. Barycki, P. Mastalerz and M. Soroka, Tetrahedron Lett. 36 (1970) 3147.
J.P. Genet, J. Uziel, M. Port, A.M. Touzin, S. Roland, S. Thorimbert and S. Tanier, Tetrahedron Lett. 33 (1992) 77
C. Qian, T. Huang, J. Org. Chem. 63 (1998) 4125
B.C. Ranu, A. Hajira and U. Jana, Org. Lett. 1 (1999) 1141
K. Manabe, S. Kobayashi, Chem. Commun. (2000) 669
S. Chandrasekhar, S.J. Prakash, V. Jagadeshwar and C. Narsihmulu, Tetrahedron Lett. 42 (2001) 5561
H. Firouzabadi, N. Iranpoor & S. Sobhani, Synthesis (2004) 2692
B. Kaboudin, M. Sorbiun, Tetrahedron Lett. 48 (2007) 9015
B. Kaboudin, E. Jafari, Synthesis (2007) 1823.
H. Schmidt, Chem. Ber. 81 (1948) 477
W.M. Linfield, E. Jungermann and A.T. Guttmann, J. Org. Chem. 26 (1961) 4088
T. Yamagishi, T. Haruki and T. Yokomatsu, Tetrahedron 62 (2006) 9210
L.A. Cates, V.S. Li, Pharm. Res. (1985) 136
A. Lecoq, A. Yiotakis and V. Dive, Synth. Commun. 24 (1994) 2877
R. Hamilton, B. Walker and B.J. Walker, Tetrahedron Lett. 36 (1995) 4451
B. Kaboudin, N. As-Habei, Tetrahedron Lett. 44 (2003) 4243
J.-L. Pirat, J. Monbrun, D. Virieux, J.-N. Volle, M. Tillard and M.H.-J. Cristau, J. Org. Chem. 70 (2005) 7035
E.A. Boyd, W.C. Chan and V.M.Jr. Loh, Tetrahedron Lett. 37 (1996) 1647
X.-Y. Jiao, C. Verbruggen, M. Borloo, W. Bollaert, A.D. Groot, R. Dommisse and A. Haemers, Synthesis (1994) 23.
J. Lewkowski, J. Organometallic Chem. 681 (2003) 225
J. Lewkowski, Heteroat. Chem. 15 (2004) 162.
B. Kaboudin, R. Nazari, Synth. Commun. 31 (2001) 2245
B. Kaboudin, M.S. Balakrishna, Synth. Commun. 31 (2001) 2773
B. Kaboudin, Tetrahedron Lett. 43 (2002) 8713
B. Kaboudin, Tetrahedron Lett. 44 (2003) 1051
B. Kaboudin, A. Rahmani, Synthesis (2003) 2705
B. Kaboudin, F. Saadati, Synthesis (2004) 1249
B. Kaboudin, A. Rahmani, Org. Prep. Proced. Int. 36 (2004) 82
B. Kaboudin, H. Haghighat, Tetrahedron Lett. 46 (2005) 7955
B. Kaboudin, H. Haghighat and T. Yokomatsu, J. Org. Chem. 71 (2006) 6604.
S. Caddick, Tetrahedron 51 (1995) 10403
A. Zlotorzynsky, Crit. Rev. Anal. Chem. 25 (1995) 43
R.S. Varma, Green Chem. (1999) 43
P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron 57 (2001) 9225
L. Perreux, A. Loupy, Tetrahedron 57 (2001) 9199
B. Kaboudin, Chem. Lett. (2001) 880
B. Kaboudin, R. Nazari, Tetrahedron Lett. 42 (2001) 8211
M.S. Balakrishna, B. Kaboudin, Tetrahedron Lett. 42 (2001) 1127
B. Kaboudin, K. Navaee, Heterocycles 55 (2001) 1443
B. Kaboudin, K. Navaee, Heterocycles 60 (2003) 2287
B. Kaboudin, F. Saadati, J. Heterocycl. Chem. 42 (2005) 699
B. Kaboudin, F. Saadati, Heterocycles 65 (2005) 353
A. Loupy, Microwaves in Organic Synthesis (2nd reprint), Wiley- VCH, Weinheim (2004).
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Professor Habib Firouzabadi on the occasion of his 65 birthday and also his retirement
Rights 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
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF03246496