RESEARCH ARTICLE

 

A facile catalyst-free Pudovik reaction for the synthesis of α-amino phosphonates

 

 

K. Reddimohan Naidu^I; K.R.K. Kumar Reddy^I; C. Vinod Kumar^I; C. Naga Raju^I; D. Divya Sharma^II

^IDepartment of Chemistry, Sri Venkateswara University, Tirupati 517 502, India
^IIDepartment of Biotechnology, Sri Padmavathi Mahila University, Tirupati 517 502, India

 

 

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ABSTRACT

Some imines were synthesized by the reaction of 5-amino 1-naphthol with substituted aromatic aldehydes in ethanol under reflux conditions. Dialkyl phosphites underwent addition with aromatic imines to give novel α-amino phosphonates. All the title compounds were characterized by elemental analysis, IR, ¹H, ¹³C, ³¹P NMR and mass spectral data. All the newly-synthesized compounds (4a-j) exhibited moderate antibacterial and antifungal activity.

Keywords: 5-Amino-1-naphthol, imines, dialkyl phosphite, α-amino phosphonates, antimicrobial activity

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Acknowledgements

The authors express their thanks to Prof. C.D. Reddy, Department of Chemistry, Sri Venkaleswara Universily, Tirupati, for his helpful guidance and discussion and also UGC-Delhi for providing financial assistance.

 

References

1 I.S. Antipin, I.l. Sloikov, E.M. Pinkhassik, N.A.Fitseva, I. Slibor and A.l. Konovalov, Tetrahedron Lett., 1997, 38, 5865-5868.         [ Links ]

2 P.A. Bartlell, J.E. Hanson and P.P. Giannousis, J. Org. Chem., 1990, 55, 6268- 6274.         [ Links ]

3 (a) M.C. Allen, W. Fuhrer, D. Tuck, R. Wade and J.M. Wood, J. Med. Chem., 1989, 32, 1652-1661;         [ Links ] (b) E.W. Logusch, D.M. Walker, J.F. McDonals, G.C. Leo and J.E. Grang, J. Org. Chem., 1988, 53, 4069-4074;         [ Links ] (c) P.P. Giannousis and P.A. Bartlell, J. Med. Chem., 1987, 30, 1603-1609.         [ Links ]

4 (a) F.R. Atherlon, C.H. Hassal and R.W. Lambert, J. Med. Chem., 1986, 29, 29-40;         [ Links ] (b) J.G.L. Allen, F.R. Atherton, C.H. Hassal, R. W. Lambert, L.J. Nisbet and P.S. Ringrose, Nature, 1978, 272, 56-58;         [ Links ] (c) J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassal, R.W. Lambert, L.J. Nisbet and P.S. Ringrose, Antimicrob. Agents Chemother., 1979, 15, 684-695;         [ Links ] (d) F.R. Atherlon, M.J. Hall, C.H. Hassal, R.W. Lamberl, W.J. Lloyd and P.S. Ringrose, Antimicrob. Agents Chemother., 1979, 15, 677-683;         [ Links ] (e) F.R. Alherlon, M.J. Hall, C.H. Hassal, R.W. Lamberl, W.J. Lloyd and P.S. Ringrose, Antimicrob. Agents Chemother., 1979, 15, 696-711.         [ Links ]

5 J. Emsley and D. Hall, The Chemistry of Phosphorus, Harper and Row, London, UK, 1976, p. 495.         [ Links ]

6 (a) R. Hirschmann, A.B. Smilh, C.M. Taylor, R.A. Benkovic, S.D. Taylor, K.M. Yager, P.A. Springler and S. Venkovic, J. Science, 1994, 265, 234;         [ Links ] (b) A.B. Smilh, C.M. Taylor, S.J. Venkovic and R. Hirschmann, Tetrahedron Lett., 1994, 35, 6853-6856.         [ Links ]

7 J.A. Sikoski, M.J. Miller, D.S. Barccolino, D.C. Cleary, S.D. Corey, J.E. Ream, D. Schnur, A. Shah and M.C. Walker, Phosphorus Sulfur Silicon, 1993, 115, 76.         [ Links ]

8 B. Slowasser, K.H. Budt, L. Jain-Qi, A. Peyman and D. Rupperl, Tetrahedron Lett, 1989, 30, 6625-6628.         [ Links ]

9 W.J. Moree, A.G. Marel, J.H. Boom and R.M.J. Liskamp, Tetrahedron, 1993, 47, 11055-11064.         [ Links ]

10 R.L. Hilderbrand and T.O. Henderson, eds., The Role of Phosphonates in Living Systems, CRC Press, Boca Raton, FL, USA, 1983.         [ Links ]

11 A.J. Kirby and S.G. Warren, The Organic Chemistry of Phosphorus, Elsevier Publishing Co, New York, NY, USA, 1967.         [ Links ]

12 A.N. Pudovik and I.V Konovalova, Synthesis, 1979, 2, 81-96.         [ Links ]

13 B.C. Ranu, A. Hajra and U. Jana, Org. Lett., 1999, 1, 1141-1143.         [ Links ]

14 (a) C. Qian and T. Huang, J. Org. Chem., 1998, 63, 4125-4128;         [ Links ] (b) S. Lee, J.H. Park, J.K. Lee and J. Kang, Chem. Commun., 2001, 1698-1699.         [ Links ]

15 F. Xu, Y. Luo, M. Deng and Q. Shen, Eur. J. Org. Chem., 2003, 24, 4728-4730.         [ Links ]

16 M.R. Saidi and N. Azizi, Synlett, 2002, 1347-1349.         [ Links ]

17 B.C. Ranu and A. Hajra, Green Chem, 2002, 4, 551-554.         [ Links ]

18 C. Thomas, The Interpretation of the Infrared Spectra of Organophosphorus Compounds, Heyden and Sons, London, UK, 1974.         [ Links ]

19 G.C.S. Reddy, B.S. Kumar, A.U.R. Sankar, M.V.N. Reddy and C.S. Reddy, J. Korean Chem. Soc., 2008, 52, 657-662.         [ Links ]

20 J. Benson, Microbiological Applications, 5th edn., W.C. Brown Publica- lions, Boslon, MA, USA, 1990.         [ Links ]

 

 

Received 6 May 2009
Revised 6 August 2009
Accepted 15 October 2009

 

 

* To whom correspondence should be addressed. E-mail: naga_raju04@yahoo.co.in