M. Anbu Kulandainathan *, K. Kulangiappar, T. Raju, A. Muthukumaran

Electro Organic Division, Central Electrochemical Research Institute, Karaikudi-630 006, India

Abstract

Azetidinone ester is the key intermediate during the synthesis of injectable cephalosporin compounds. This intermediate is undergoing electrochemical reaction during the process of conversion from penicillin to cephalosporin. The CV and RRDE studies clearly indicate that electro-reduction of this compound is taking place in three steps under the condition. The first two peaks correspond to the two, one electron transfers and the third one is due to the proton addition from the non-aqueous solvent. And during the process, the cyclisation is also taking place in order to neutralise the charge. Further CV and RRDE studies with the addition of small amount of water to the above system clearly confirm the mechanism. This was very well confirmed by the FTIR analysis of the product obtained from the bulk electrolysis.

Keywords: azetidinone ester, electro reduction, cyclic voltammetry, RRDE, electrode kinetics.

Texto disponível em PDF

Full text only in PDF format

References

1.       P. Zelenay, V. Menon, H. Zhang, C.R. Martin, D. Walker, J. Lee, E. Bernasconi, L. Sogli, Electrochemical Soc., Proceedings 97-7 (1997) 45.        [ Links ]

2.       “Recent advances in the chemistry of b-lactam antibiotics”, Ed. By J. Elks, Chem. Soc. Burlington House, London (1977), p.101.        [ Links ]

3.       S. Karady, L.N. Weinstock, F.E. Roberts, J. Ten Broeke, R.F. Shuman, A.M. Hoinowski, S.H. Pines, M. Sletzinger, Tetrahedron Lett. 17 (1976) 2404.        [ Links ]

4.       S. Torii, H. Tanaka, N. Tada, S. Nagao, M. Sasaoka, Chem. Lett. (1984) 877.        [ Links ]

5.       S. Torii, H. Tanaka, T. Siroi, Tetrahedron Lett. 23 (1982) 2187.        [ Links ]

6.       P.M. Bersier, L. Carlsson, J. Bersier, 10^th International Forum on Applied Electrochemistry, Sand Key, Florida, November 1996.        [ Links ]

7.        I.F. Jones, J.E. Page, C.T. Rhodes, J. Pharmac. 20  (1968) 45S.        [ Links ]

8.       M. Ochiai, O. Aki, A. Morimoto, T. Okada, K. Shinozaki, Y. Ashi, Tetrahedron Lett. 23 (1972) 2341.        [ Links ]

9.       M. Ochiai, O. Aki, A. Morimoto, T. Okada, T. Kaneko, Y. Ashi, Tetrahedron Lett. 23 (1972) 2345.        [ Links ]

10.     D.A. Hall, J. Pharm. Sci. 62 (1973) 980.        [ Links ]

11.     J.E. Baldwin, R.M. Adlington, N.P. Cronch, I.A.C. Pereira, Tetrahedron 9 (1993) 4907.        [ Links ]

12.     V.G. Levich, “Physicochemical Hydrodynamics”, Prentice Hall: Englewood Cliffs, NJ, 1962.        [ Links ]

13.     A.J. Bard, L.R. Faulkner, “Electrochemical Methods: Fundamentals and Applications”, John Wiley, N.Y., 1980, Chapter 11.        [ Links ]

14.     J.P. Petrovich, J.D. Anderson, M.M. Baizer, J. Org. Chem. 31 (1966) 3897.        [ Links ]

15.     S. Torii, 7^th Int. Forum, Electrolysis in the Chemical Industry, Buena Vista, Nov. 7-11, 1993.        [ Links ]

16.     F. D’Souza, J. Choi, W. Kutner, J. Phys. Chem. B 102 (1998) 4247.        [ Links ]

* Corresponding author. E-mail address: manbu123@yahoo.com