A one-pot double C-H activation palladium catalyzed route to a unique class of highly functionalized thienoisoquinolines

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2738-2741

  Wong, Nicholas W Y ^a,b   Forgione, Pat ^a,b  

^a Dept of Electrical and Computer Engineering   (Canada)

^b Centre for Green Chemistry and Catalysis   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PALLADIUM; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; INDOLES; ISOQUINOLINES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; THIOPHENES;

EID: 84861800066     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3009655     Document Type: Article

References (43)

1. Cooper, T. W.; Campbell, I. B.; Macdonald, S. J. F. Angew. Chem., Int. Ed. 2010, 49, 8082
2. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337
3. Deng, H.; Hu, H.; He, M.; Hu, J.; Niu, W.; Ferrie, A. M.; Fang, Y. J. Med. Chem. 2011, 54, 7385
4. Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Alcaro, S.; Ortuso, F.; Yánez, M.; Orallo, F.; Cirilli, R.; Ferretti, R.; La Torre, F. J. Med. Chem. 2008, 51, 4874
5. Lipinski, C. A.; Lombardo, F.; Dominv, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 2001, 46, 3
6. Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451
7. Köster, H.; Crann, T.; Brass, S.; Herhaus, C.; Zentgraf, M.; Neumann, L.; Heine, A.; Klebe, G. J. Med. Chem. 2011, 54, 7784
8. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359
9. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461
10. Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440
11. Wang, Y.; Ai, J.; Wang, Y.; Chen, Y.; Wang, L.; Liu, G.; Geng, M.; Zhang, A. J. Med. Chem. 2011, 54, 2127
12. Oster, A.; Hinsberger, S.; Werth, R.; Marchais-Oberwinkler, S.; Frotscher, M.; Hartmann, R. W. J. Med. Chem. 2010, 53, 8176
13. Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253
14. Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266
15. Campeau, L.-C.; Bertrand-Laperle, M.; Leclerc, J.-P.; Villemure, E.; Gorelsky, S.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3276
16. Satoh, T.; Kametani, Y.; Terao, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740
17. Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046
18. Liégault, B.; Lapointe, D.; Caron, L.; Vlassova, A.; Fagnou, K. J. Org. Chem. 2009, 74, 1826
19. Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250
20. Karthikeyan, J.; Cheng, C.-H. (2011, 50, 9880.
21. Derridj, F.; Roger, J.; Djebbar, S.; Doucet, H. Org. Lett. 2010, 12, 4320
22. Chen, L.; Bruneau, C.; Dixneuf, P. H.; Doucet, H. Green Chem. 2012, 14, 1111
23. Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362
24. Ackermann, L.; Vincente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
25. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
26. Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11351
27. Dong, J. J.; Doucet, H. Eur. J. Org. Chem. 2010, 611
28. Coghlan, R. D.; Fobare, W. F.; Trybulski, E. J. Thienoisoquinoline- Phenylsulfonamides and Their Use as ER-NFkappaB Inhibitors, U.S. 2006/0154875, Wyeth (2006).
29. Ueda, K.; Yanagisawa, S.; Yamaguchi, J.; Itami, K. Angew. Chem., Int. Ed. 2010, 49, 8946
30. For a recent review, see: Cornella, J.; Larrosa, I. Synthesis 2012, 44, 653
31. Gooßen, L. J.; Zimmermann, B.; Knauber, T. Angew. Chem., Int. Ed. 2008, 47, 7103
32. Goossen, L. J.; Rodríguez, N.; Lange, P. P.; Linder, C. Angew. Chem., Int. Ed. 2010, 49, 1111
33. Lange, P. P.; Goossen, L. J.; Podmore, P.; Underwood, T.; Sciammetta, N. Chem. Commun. 2011, 47, 3628
34. Goossen, L. J.; Linder, C.; Rodríguez, N.; Lange, P. P. Chem.-Eur. J. 2009, 15, 9336
35. Goossen, L. J.; Lange, P. P.; Rodríguez, N.; Linder, C. Chem.-Eur. J. 2010, 16, 3906
36. Goossen, L. J.; Rodríguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824
37. Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
38. Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323
39. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250
40. Becht, J.-M.; Le Drian, C. Org. Lett. 2008, 10, 3161
41. Bilodeau, F.; Brochu, M.-C.; Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550
42. Mitchell, D.; Coppert, D. M.; Moynihan, H. A.; Lorenz, K. T.; Kissane, M.; McNamara, O. A.; Maguire, A. R. Org. Process Res. Dev. 2011, 15, 981
43. Zinchenko, S. Y.; Efimenko, R. A.; Suikov, S. Y.; Kobrakov, K. I.; Bogza, S. L. Chem. Heterocycl. Compd. 2009, 45, 365