Application of daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines

Organic Letters

Volumn 11, Issue 7, 2009, Pages 1511-1514

  Yotphan, Sirilata ^a   Bergman, Robert G ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAZEPINE DERIVATIVE; COPPER; CUPROUS IODIDE; IODIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BENZAZEPINES; CATALYSIS; COPPER; IODIDES; MOLECULAR STRUCTURE;

EID: 64349102735     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900103a     Document Type: Article

References (24)

1. (a) Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S. J. Med. Chem. 1988, 31, 2235.
2. (b) Patchett, A. A.; Nargund, R. P. Annu. Rep. Med. Chem. 2000, 35, 289.
3. For recent reviews, see: (1) Leonard, B. E. Hum. Psycopharmacol. Clin. Exp. 1999, 14, 125. 2 Fryer, R. I. Bicyclic Diazepines. The Chemistry of Heterocyclic Compounds; Wiley: New York, 1991; Chapter 7.
4. (a) McDonald, I. M.; Austin, C.; Buck, I. M.; Dunstone, D. J.; Gaffen, J.; Griffin, E.; Harper, E. A.; Hull, R. A. D.; Kalindjian, B.; Linney, I. D.; Low, C. M. R.; Patel, D.; Pether, M. J.; Raynor, M.; Roberts, S. P.; Shaxted, M. E.; Spencer, J.; Steel, K. O. M.; Sykes, D. A.; Wright, P. T.; Xun, W. J. Med. Chem. 2007, 50, 4789.
5. (b) McDonald, I. M.; Black, J. W.; Buck, I. M.; Dunstone, D. J.; Griffin, E. P.; Haper, E. A.; Hull, R. A. D.; Kalindjian, B.; Lilley, E. J.; Linney, I. D.; Pater, M. J.; Roberts, S. P.; Shaxted, M. E.; Spencer, J.; Steel, K. I. M.; Sykes, D. A.; Walker, M. K.; Watt, G. F.; Wright, L.; Wright, P. T.; Xun, W. J. Med. Chem. 2007, 50, 3101.
6. For recent references, see: (a) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997.
7. (b) Tucker, H.; Le Count, D. J. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Amsterdam, 1996; Vol. 9, p 151.
8. (c) del Pozo, C.; Macias, A.; Alonso, E.; Gonzalez, J. Synthesis 2004, 16, 2697.
9. (d) Neamati, N.; Turpin, J. A.; Winslow, H. E.; Chrisensen, J. L.; Williamson, K.; Orr, A.; Rice, W. G.; Pommier, Y.; Garofalo, A.; Brizzi, A.; Campiani, G.; Fiorini, I.; Nacci, V. J. J. Med. Chem. 1999, 42, 3334.
10. (e) Nadin, A.; Sanchez Lopez, J. M.; Owens, A. P.; Howells, D. M.; Talbot, A. C.; Harrison, T. J. Org. Chem. 2003, 68, 2844.
11. (f) Spencer, J.; Chowdhry, B. Z.; Mallet, A. I.; Rathnam, R. P.; Adatia, T.; Bashall, A.; Rominger, F. Tetrahedron 2008, 64, 6082.
12. (a) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
13. (b) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332.
14. (c) Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.
15. Gribble, M. W.; Ellman, J. A.; Bergman, R. G. Organometallics 2008, 27, 2152.
16. For recent reviews on C-H functionalization of heterocycles, see: (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
17. (b) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
18. (c) Campeau, L.-C.; Fragnou, K. Chem. Commun. 2006, 1253.
19. See Supporting Informationfor experimental details of substrate preparation and screening of reaction conditions.
20. (a) Do, H.-Q.; Kashif Khan, R. M.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185.
21. (b) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128.
22. (c) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
23. For other reports on copper-catalyzed and copper-mediated C-H bond functionalization and C-C bond formation of heterocycles, see: (a) Besselievre, F.; Piguel, S.; Mahuteau-Betzer, F.; Grierson, D. S. Org. Lett. 2008, 10, 4029.
24. (b) Yoshizumi, T.; Tsurugi, H.; Satoh, T.; Miura, M. Tetrahedron Lett. 2008, 49, 1598.