Synthesis of thiophene-based TAK-779 analogues by C-H arylation

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5579-5586

  Junker, Anna ^a   Yamaguchi, Junichiro ^b   Itami, Kenichiro ^b,c   Wünsch, Bernhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b NAGOYA UNIVERSITY   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; CATALYSTS; CHEMICAL REACTIONS;

BUILDING BLOCKES; C-H ARYLATION; CATALYST SYSTEM; DIVERSIFICATION STRATEGIES; ELECTRON-DEFICIENT; ELECTRON-RICH; PRIMARY AMINES; RAPID SYNTHESIS;

THIOPHENE;

N [4 [[[6,7 DIHYDRO 2 (4 METHYLPHENYL) 5H BENZOCYCLOHEPTEN 8 YL]CARBONYL]AMINO]BENZYL] N,N DIMETHYL 2H TETRAHYDROPYRAN 4 AMINIUM CHLORIDE; POLYCYCLIC AROMATIC HYDROCARBON; THIOPHENE;

AMIDATION; ARTICLE; ARYLATION; CATALYST; HYDROLYSIS; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84879297703     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400692p     Document Type: Article

References (27)

1. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. J. Enzyme. Inhib. Med. Chem. 2002, 17, 69
2. Shiraishi, M.; Aramaki, Y.; Seto, M.; Imoto, H.; Nishikawa, Y.; Kanzaki, N.; Okamoto, M.; Sawada, H.; Nishimura, O.; Baba, M.; Fujino, M. J. Med. Chem. 2000, 43, 2049
3. Pau, A.; Murineddu, G.; Asproni, B.; Murruzzu, C.; Grella, G. E.; Pinna, G. A.; Curzu, M. M.; Marchesi, I.; Bagella, L. Molecules 2009, 14, 3494
4. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077
5. Shibahara, F.; Yamaguchi, E.; Murai, T. Chem. Commun. 2010, 46, 2471
6. Meyer, C.; Schepmann, D.; Yanagisawa, S.; Yamaguchi, J.; Itami, K.; Wünsch, B. Eur. J. Org. Chem. 2012, 2012, 5972
7. Meyer, C.; Schepmann, D.; Yanagisawa, S.; Yamaguchi, J.; Dal Col, V.; Laurini, E.; Itami, K.; Pricl, S.; Wünsch, B. J. Med. Chem. 2012, 55, 8047
8. Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. Tetrahedron 2008, 64, 6073
9. Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 126, 11748
10. Colby, D. A.; Robert, G.; Bergman, R. G.; Ellman Jonathan, A. Chem. Rev. 2010, 110, 624
11. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
12. Canivet, J.; Yamaguchi, J.; Ban, I.; Itami, K. Org. Lett. 2009, 11, 1733
13. Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 1737
14. Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 169
15. Amaike, K.; Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 13573
16. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
17. Arai, N.; Miyaoku, T.; Teruya, S.; Mori, A. Tetrahedron Lett. 2008, 49, 1000
18. Chen, L.; Bruneau, C.; Dixneuf, P. H.; Doucet, H. Tetrahedron 2013, 69, 4381
19. Bellina, F.; Rossi, R. Tetrahedron 2009, 65, 10269
20. Yanagisawa, S.; Ueda, K.; Sekizawa, H.; Itami, K. J. Am. Chem. Soc. 2009, 131, 14622
21. Yanagisawa, S.; Itami, K. Tetrahedron 2011, 67, 4425
22. Join, B.; Yamamoto, T.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 3644
23. Crabtree, R. H.; Davis, M. W. Organometallics 1983, 2, 681
24. Evans, D. A.; Fu, G. C. J. Am. Chem. Soc. 1991, 113, 4042
25. Garcia-Melchor, M.; Gorelsky, S. I.; Woo, T. K. Chemistry 2011, 17, 13847
26. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118
27. Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754