Ceric ammonium nitrate on silica gel for solid-solid phase N-dearylation of -lactams

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 184, Issue 7, 2009, Pages 1738-1749

  Jarrahpour, Aliasghar ^a   Zarei, Maaroof ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

2 Azetidinones; Ceric ammonium nitrate; N dearylation; N unsubstituted lactam; Solid solid phase; Solvent free

Indexed keywords

EID: 70449724716     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500802336630     Document Type: Article

References (52)

1. K. Smith, Ed., Solid Supports and Catalysis in Organic Synthesis (Ellis Horwood, New York, 1992).
2. V. K. Yadav and K. K. Kapoor, Tetrahedron Lett., 35, 9481-9484 (1994).
3. A. K. Banerjee, M. S. L Mimo, and W. Vera Vegas, Russ. Chem. Rev., 70, 971-990 (2001).
4. F. Toda, Acc. Chem. Res., 28, 480-486 (1995).
5. G. W. V. Cave, C. L. Raston, and J. L. Scott, Chem. Commun., 2159-2169 (2001).
6. F. Toda and K. Tanaka, Chem. Rev., 100, 1025-1074 (2000).
7. A. Basak, K. Chandra, R. Pal, and S. C. Ghosh, Synlett, 1585-1588 (2007).
8. (a) R. B. Morin and H. Gorman, Ed., Chemistry and Biology of â-Lactam Antibiotics (Acadamic Press, New York, 1982), Vol 1;
9. (b) P. G. Sammes, Ed., Topics in Antibiotic Chemistry (Ellis Horwood Ltd., New York, 1980), Vol.3;
10. (c) J. O'Sullivan and E. P. Abraham, Antibiotics (Springer-Verlag, Berlin, 1981), Vol.IV;
11. (d) G. Lukacs and M. Ohno, Eds., Recent Progress in the Chemical Synthesis of Antibiotics (Springer, Berlin, 1990).
12. (a) R. M. Adlington, J. E. Baldwin, B. Chen, S. L. Cooper,W.McCoull, G. J. Pritchard, T. J. Howe, G.W. Becker, R. B. Hermann, A. M. McNulty, and B. L.Neubauer, Bioorg. Med. Chem. Lett., 7, 1689-1694 (1997);
13. (b) J. C. Sutton, S. A. Bolton, K. S. Harti, M. H. Huang, G. Jacobs, W. Meng, G. Zhao, and G. S. Bisacchi, Bioorg. Med. Chem. Lett., 14, 2233-2239 (2004);
14. (c) R. Gonzalez-Muniz, E. De Clercq, J. Balzarini, G. G. Navarro, J. P. De Vega, and C. Anderi, Bioorg. Med. Chem. Lett., 14, 2253-2256 (2004);
15. (d) J. Tozsera, T. Sperka, J. Pitlik, and P. Bagossia, Bioorg. Med. Chem. Lett., 15, 3086-3090 (2005);
16. (e) J. Marchand-Brynaert, G. Dive, M. Galleni, and and S. Gerard, Bioorg. Med. Chem., 12, 129-138 (2004);
17. (f) X. Bai, X. Xu, R. Fu, J. Chen, and S. Chen, Bioorg. Med. Chem. Lett., 17, 101-104 (2007);
18. (g) K. G. Desai and K. R. Desai, Bioorg. Med. Chem., 14, 8271-8279 (2006);
19. (h) B. K. Banik, F. F. Becker, and I. Banik, Bioorg. Med. Chem., 13, 3611-3622 (2005).
20. (a) B. Alcaide, P. Almendros, and C. Aragoncillo, Chem. Rev., 107, 4437-4492 (2007);
21. (b) B. Alcaide and P. Almendros, Synlett, 381-393 (2002);
22. (c) B. Alcaide and P. Almendros, Chem. Soc. Rev., 30, 226-240 (2001);
23. (d) I. Ojima, Acc. Chem. Res., 28, 383-389 (1995).
24. (a) H. Ge, J. T. Spletstoser, Y. Yang, M. Kayser, and G. I. Georg, J. Org. Chem., 72, 756-759 (2007);
25. (b) M. Suffness, Taxol Science and Applications (CRC Press, Boca Raton, FL, USA, 1995).
26. F. P. Cossio, B. Lecea, and C. Palomo, J. Chem. Soc., Chem. Commun., 1743-1744 (1987).
27. (a) E. Bandini, G. Favi, G. Martelli, M. Panunzio, and G. Piersanti, Org. Lett., 2, 1077-1079 (2000);
28. (b) D. J. Hart, K.-I. Kanai, D. G. Thomas, and T.-K. Yang, J. Org. Chem., 48, 289-294 (1983).
29. (a) A. Jarrahpour and M. Zarei, Molecules, 12, 2364-2379 (2007);
30. (b) P. Imbach, M. Lang, C. Garcia-Echeverria, V. Guagnano, M. Noorani, J. Roesel, F. Bitsch, G. Rihs,and P. Furet, Bioorg. Med. Chem. Lett., 17, 358-362 (2007);
31. (c) E. Turos, B. Heldreth, T. E. Long, Jang, G. S. K. Reddy, S. Dickeyb, and D. V. Lim, Bioorg. Med. Chem., 14, 3775-3784 (2006);
32. (d) P. Del Buttero, G. Molteni, and T. Pilati, Tetrahedron, 61, 2413-2419 (2005);
33. (e) R. Annunziata, M. Benaglia, M. Cinquini, and F. Cozzi, J. Org. Chem., 68, 2952-2955 (2003);
34. (f) J. Podlech and M. R. Linder, J. Org. Chem., 62, 5873-5883 (1997);
35. (g) K. Karupaiyan, V. Srirajan, A. R. A. S. Deshmukh, and B. M. Bhawal, Tetrahedron Lett., 38, 4281-4284 (1997).
36. (a) X.-G. Li and L. T. Kanerva, Adv. Synth. Catal., 348, 197-205 (2006);
37. (b) M. Ishiguro, R. Tanaka, K. Namikawa, T. Nasu, H. Inoue, T. Nakatsuka, Y. Oyama, and S. Imajo, J. Med. Chem., 40, 2126-2132 (1997).
38. T.W.Green and P. G. M. Wuts, Green's Protective Group in Organic Synthesis (John Wiley & Sons, New Jersey, 2007), 4th ed., p. 903.
39. D. K. Kronenthal, C. Y. Han, and M. K. Taylor, J. Org. Chem., 47, 2765-2768 (1982).
40. J. C. Sutton, S. A. Bolton, K. S. Hartl, M.-H. Huang, G. Jacobs, W. Meng, M. L. Ogletree, Z. Pi, W. A. Schumacher, S. M. Seiler, W. A. Slusarchyk, U. Treuner, R. Zahler, G. Zhao, and G. S. Bisacchi, Bioorg. Med. Chem. Lett., 12, 3229-3233 (2002).
41. (a) J. R.Hwu,M. L. Jain, F.-Y. Tsai, S.-C. Tsay, A. Balakumar, and G. H. Hakimelahi, J. Org. Chem., 65, 5077-5088 (2000);
42. (b) M. H. Ali, M. Niedbalski, G. Bohnert, and D. Bryant, Synth. Commun., 36, 1751-1759 (2006);
43. (c) A. Fisher and G. N. Henderson, Synthesis, 641-643 (1985);
44. (d) H. M. Chawla and R. S. Mittal, Synthesis, 70-72 (1985);
45. (e) M. Chakrabarty and A. Batabyal, Synth. Commun., 24, 1-10 (1994).
46. A. Jarrahpour and M. Zarei, Synlett, 381-385 (2008).
47. A. Jarrahpour and M. Zarei, Synth. Commun., 1837-1845 (2008).
48. (a) H. Staudinger, Liebigs Ann. Chem., 356, 51-123 (1907);
49. (b) A. Jarrahpour and D. Khalili, Tetrahedron Lett., 48, 7140-7143 (2007);
50. (c) A. Jarrahpour and M. Zarei, Molecules, 11, 49-58 (2006).
51. T. W. Green and P. G. M. Wuts, Protective Group in Organic Synthesis (John Wiley & Sons, New York, 1999), 3rd ed., p. 637.
52. K. V. N. S. Srinivas and B. Das, J. Chem. Res., 556-557 (2002).