Synthesis of diazepinones via intramolecular transamidation

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3361-3364

  Vasudevan, Anil ^a   Villamil, Clara I ^a   Djuric, Stevan W ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; DIAZEPINE DERIVATIVE;

AMIDATION; ARTICLE; CHIRALITY; MOLECULAR DYNAMICS; STEREOCHEMISTRY; SYNTHESIS;

EID: 4644245828     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048638t     Document Type: Article

References (32)

1. Schreiber, S. L. Science 2000, 287, 1964.
2. (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
3. (b) Winkler, J. D. Chem. Rev. 1996, 96, 167.
4. (c) Inanaga, K.; Takasu, K.; Ihara, M. J. Am. Chem. Soc. 2004, 126(5), 1352.
5. (d) Padwa, A., Pearson, W. H., Eds. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Wiley: New York, 2002; p 59.
6. (a) Belanger, G.; Deslongchamps, P. J. Org. Chem. 2000, 65, 7070.
7. (b) Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709.
8. (c) Brooking, P.; Crawshaw, M.; Hird, N. W.; Jones, C.; MacLachlan, W. S.; Readshaw, S. A.; Wilding, S. Synthesis 1999, 1986.
9. Staudinger, H. Liebigs Ann. Chem. 1907, 356, 51.
10. Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253.
11. Liu, Y.; McWhorter, W. J. Am. Chem. Soc. 2003, 125, 4240.
12. Breitenlechner, C. B.; Wegge, T.; Berillon, L.; Graul, K.; Marzenell, K.; Friebe, W.; Thomas, U.; Schumacher, R.; Huber, R.; Engh, R. A.; Masjost, B. J. Med. Chem. 2004, 47 (6), 1375.
13. (a) Nubbemeyer, U. Top. Curr. Chem. 2001, 216, 125.
14. (b) Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131.
15. Bosch, I.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671.
16. (a) Bieräugel, H.; Jansen, P. T.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2002, 4, 2673.
17. (b) Bieräugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Org. Biomol. Chem. 2003, 1, 1830.
18. David, O.; Meester, W. J.; Bieraeugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Angew. Chem., Int. Ed. 2003, 42 (36), 4373.
19. (a) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martinez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360.
20. (b) Palomo, C.; Aizpurua, J. M.; Garcia, J. M.; Galarza, R.; Legido, M.; Urchegui, R.; Roman, P.; Luque, A.; Server-Carrio, J.; Linden, A. J. Org. Chem. 1997, 62, 2070.
21. (c) Palomo, C.; Ganboa, I.; Cuevas, C.; Boschetti, C.; Linden, A. Tetrahedron Lett. 1997, 38 (26), 4643.
22. Evans, D.; Sjogren, E. Tetrahedron Lett. 1985, 26 (32), 3783.
23. (a) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582.
24. (b) Strauss, C. R. Aust. J. Chem. 1999, 52, 83.
25. (c) Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Org. Lett. 2003, 5(12), 2131.
26. (d) Larhead, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406.
27. (e) Commercial vendors of single-mode microwave instrumentation include Biotage AB (www.biotage.com) and CEM (www.cem.com).
28. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley-Interscience: Hoboken, NJ, 1999.
29. Teague, S. J.; Davis, A. M.; Leeson, P. D.; Oprea, T. Angew. Chem., Int. Ed. 1999, 38 (24), 3743.
30. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Raimondi, L. Tetrahedron 1994, 50 (31), 9471.
31. During the course of this work, two reports describing the use of β-lactams as useful precursors for the synthesis of macrolactams have appeared, (a) Banfi, L.; Guanti, G.; Rasparini, M. Eur. J. Org. Chem. 2003, 7, 1319. (b) Klapars, A.; Parris, S.; Anderson, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126 (11), 3529.
32. During the course of this work, two reports describing the use of β-lactams as useful precursors for the synthesis of macrolactams have appeared, (a) Banfi, L.; Guanti, G.; Rasparini, M. Eur. J. Org. Chem. 2003, 7, 1319. (b) Klapars, A.; Parris, S.; Anderson, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126 (11), 3529.