New reactions of functionalized β-lactams

Pure and Applied Chemistry

Volumn 77, Issue 12, 2005, Pages 2061-2071

  Van Brabandt, Willem ^a   Dejaegher, Yves ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

lactams; Alkenoates; Azetidines; Azetines; Aziridines; Bicyclic lactams

Indexed keywords

EID: 29244476042     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200577122061     Document Type: Conference Paper

References (39)

1. (a) M. I. Page. Acc. Chem. Res. 17, 144 (1984);
2. (b) M. I. Page. Adv. Phys. Org. Chem. 23, 165 (1987);
3. (c) M. I. Page and A. P. Laws. Tetrahedron 56, 5631 (2000).
4. (a) D. A. Burnett, M. A. Caplan, H. R. Davis, Jr., R. E. Burrier, J. W. Clader. J. Med. Chem. 37, 1733 (1994);
5. (b) J. W. Clader, D. A. Burnett, M. A. Caplan, M. S. Domalski, S. Dugar, W. Vaccaro, R. Sher, M. E. Browne, H. Zhao, R. E. Burner, B. Salisbury, H. R. Davis, Jr. J. Med. Chem. 39, 3684 (1996);
6. (c) W. D. Vaccaro, R. Sher, H. R. Davis, Jr. Bioorg. Med. Chem. Lett. 8, 35 (1998).
7. W. T. Han, A. K. Trehan, J. J. K. Wright, M. E. Federici, S. M. Seiler, N. A. Meanwell. Bioorg. Med. Chem. 3, 1123 (1995).
8. P. R. Bonneau, F. Hasani, C. Plouffe, E. Malenfant, S. R. LaPlante, I. Guse, W. W. Ogilvie, R. Plante, W. C. Davidson, J. L. Hopkins, M. M. Morelock, M. G. Cordingley, R. Déziel. J. Am. Chem. Soc. 121, 2965 (1999).
9. V. Güner, S. Yildirir, B. Özçelik, U. Abbasoglu. Il Farmaco 55, 147 (2000).
10. (a) P. Palomo, J. M. Aizpura, I. Ganboa, M. Oiarbide. Eur. J. Org. Chem. 3223 (1999);
11. (b) G. S. Singh. Tetrahedron 59, 7631 (2003).
12. (a) J. E. Baldwin. J. Chem. Soc., Chem. Commun. 734 (1976);
13. (b) J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman, R. C. Thomas. J. Chem. Soc., Chem. Commun. 736 (1976);
14. (c) J. E. Baldwin. J. Chem. Soc., Chem. Commun. 738 (1976);
15. (d) J. E. Baldwin and L. I. Kruse. J. Chem. Soc., Chem. Commun. 233 (1977).
16. (a) I. Ojima. Acc. Chem. Res. 28, 383 (1995);
17. (b) J. M. Axten, L. Krim, H. F. Kung, J. D. Winkler. J. Org. Chem. 63, 9628 (1998);
18. (c) J. Cheng and T. J. Deming. J. Am. Chem. Soc. 123, 9457 (2001).
19. (a) Y. L. Chen, C.-W. Chang, K. Hedberg. Tetrahedron Lett. 27, 3449 (1986);
20. (b) M. I. Page, P. Webster, S. Bogdan, B. Tremerie, L. Ghosez. J. Chem. Soc., Chem. Commun. 318 (1987);
21. (c) M. I. Page, P. Webster, L. Ghosez, S. Bogdan. Bull. Soc. Chim. Fr. 272 (1988);
22. (d) S. A. Deraniyagala, S. A. Adediran, R. F. Pratt. J. Org. Chem. 60, 1619 (1995);
23. (e) A. Llinás, B. Vilanova, J. Frau, F. Muñoz, J. Donoso, M. I. Page. J. Org. Chem. 63, 9052 (1998);
24. (f) N. Díaz, D. Suárez, T. L. Sordo. J. Org. Chem. 64, 3281 (1999);
25. (g) N. Díaz, D. Suárez, T. L. Sordo. J. Org. Chem. 64, 9144 (1999);
26. (h) N. Díaz, D. Suárez, T. L. Sordo. J. Am. Chem. Soc. 122, 6710 (2000).
27. See also Y. Dejaegher and N. De Kimpe. J. Org. Chem. 69, 5974 (2004).
28. S. N. Rao and R. A. M. O'Ferrall. J. Org. Chem. 55, 3244 (1990).
29. (a) N. H. Cromwell and B. Phillips. Chem. Rev. 79, 331 (1979);
30. (b) J. A. Moore and R. S. Ayers. In Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, A. Hassner (Ed.), Part 2, pp. 1-217, John Wiley, New York (1983);
31. (c) D. E. Davies and R. C. Starr. In Comprehensive Heterocyclic Chemistry, Vol. 7, Part 5, W. Lwowski (Ed.), pp. 237-284, Pergamon, Oxford (1984);
32. (d) N. De Kimpe. In Comprehensive Heterocyclic Chemistry II, Vol. 1, A. Padwa (Ed.), Chap. 1.21, Three- and four-membered rings, with all fused systems containing three- and four membered rings. Elsevier, Oxford (1996).
33. I. Ojima, T. Yamamoto, K. Nakahashi, M. Yamashita, R. Abe. J. Org. Chem. 56, 5263 (1991).
34. (a) M. Yamashita and I. Ojima. J. Am. Chem. Soc. 105, 6339 (1983);
35. (b) I. Ojima, T. Yamamoto, K. Nakahashi. Tetrahedron Lett. 26, 1761 (1985);
36. (c) I. Ojima, K. Nakahashi, S. Brandstadter, N. Hatanaka. J. Am. Chem. Soc. 109, 1798 (1987).
37. (a) A. Hassner and N. Wiegand. J. Org. Chem. 51, 3652 (1986);
38. (b) A. Hassner and N. Murty. Tetrahedron Lett. 28, 683 (1987);
39. (c) A. Hassner and N. Murty. Tetrahedron Lett. 28, 4097 (1987).