Concise copper-catalyzed synthesis of tricyclic biaryl ether-linked aza-heterocyclic ring systems

Organic Letters

Volumn 15, Issue 21, 2013, Pages 5448-5451

  Mestichelli, Paola ^a   Scott, Matthew J ^a   Galloway, Warren R J D ^a   Selwyn, Jamie ^a   Parker, Jeremy S ^b   Spring, David R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; ETHER DERIVATIVE; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AZA COMPOUNDS; CATALYSIS; COPPER; ETHERS; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE;

EID: 84887075918     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4025259     Document Type: Article

References (26)

1. Wang, L.; Sullivan, G. M.; Hexamer, L. A.; Hasvold, L. A.; Thalji, R.; Przytulinska, M.; Tao, Z.; Li, G.; Chen, Z.; Xiao, Z.; Gu, W.; Xue, J.; Bui, M.; Merta, P.; Kovar, P.; Bouska, J. J.; Zhang, H.; Park, C.; Stewart, K. D.; Sham, H. L.; Sowin, T. J.; Rosenberg, S. H.; Lin, N. J. Med. Chem. 2007, 50, 4162
2. Klunder, J. M.; Hargrave, K. D.; West, M.; Cullen, E.; Pal, K.; Behnke, M. L.; Kapadia, S. R.; McNeil, D. W.; Wu, J. C.; Chow, G. C. J. Med. Chem. 1992, 35, 1887
3. Lu, S. M.; Maggi, C. A.; Gensini, M.; Bigioni, M.; Parlani, M.; Giolitti, A.; Fratelli, M.; Valli, C.; Terao, M.; Garattini, E. ACS Med. Chem. Lett. 2010, 1, 411
4. David, J.; Grewal, R. S. Indian J. Exp. Biol. 1974, 12, 225
5. Jiang, X. L.; Lee, G. T.; Prasad, K.; Repic, O. Org. Process Res. Dev. 2008, 12, 1137
6. Sakaki, J.; Konishi, K.; Kishida, M.; Gunji, H.; Kanazawa, T.; Uchiyama, H.; Fukaya, H.; Mitani, H.; Kimura, M. Bioorg. Med. Chem. Lett. 2007, 17, 4808
7. Ebisawa, M.; Umemiya, H.; Ohta, K.; Fukasawa, H.; Kawachi, E.; Christoffel, G.; Gronemeyer, H.; Tsuji, M.; Hashimoto, Y.; Shudo, K.; Kagechika, H. Chem. Pharm. Bull 1999, 47, 1778
8. Chakrabarti, A.; Bagnall, A. M.; Chue, P.; Fenton, M.; Palaniswamy, V.; Wong, W.; Xia, J. Loxapine for schizophrenia. Cochrane Database of Systematic Reviews 2007, Issue 4, Art. No. CD001943.
9. Ouyang, X.; Chen, Z.; Liu, L.; Dominguez, C.; Kiselyove, A. S. Tetrahedron 2000, 56, 2369
10. Ouyang, X.; Kiselyove, A. S. Tetrahedron Lett. 1999, 40, 5827
11. Ohgog, T.; Tanaka, S.; Fujimoto, M.; Kitahara, A. Yakugaku Zassi 1977, 97, 24
12. Tanaka, S.; Hashimoto, K. 6-substituierte 6,7-dihydro-5H-dibenzo b.g. 1.5 Oxazocine und Thiazocine und Verfahren zu deren Herstellung. Ger. Offen. DE 2044508, May 1971.
13. Joergensen, T. K.; Andersen, K. E.; Andersen, H. S.; Hohlweg, R.; Madsen, P.; Olsen, U. B. Novel Heterocyclic Compounds. WO 9631497 A1, October 1996.
14. Rousseau, G. Tetrahedron 1995, 51, 2777
15. Surry, D.; Su, X.; Fox, D. J.; Franckevicius, V.; Macdonald, S. J. F.; Spring, D. R. Angew. Chem., Int. Ed. 2005, 44, 1870
16. Surry, D. S.; Spring, D. R. Chem. Soc. Rev. 2005, 2589
17. Tanaka, S.; Hashimoto, K.; Tanaka, S.; Hashimoto, K. Yakugaku Zassi 1973, 93, 1003
18. Tanaka, S.; Hashimoto, K.; Wantanabe, H. Chem. Pharm. Bull. 1973, 21, 1683
19. Tanaka, S.; Hashimoto, K. US Patent 3803143, April 1974.
20. Lieb, F.; Eiter, K. Liebigs Ann. Chem 1976, 93, 203
21. Kenwright, J. L.; Galloway, W. R. J. D.; Blackwell, D. T.; Isidro-Llobet, A.; Hodgkinson, J.; Wortmann, L.; Bowden, S. D.; Welch, M.; Spring, D. R. Chem.-Eur. J. 2011, 17, 2981
22. A similar chelate effect for enabling medium-ring biaryl synthesis using carbon-hydrogen coupling has previously been reported; see: Pintori, D. G.; Greaney, M. F. J. Am. Chem. Soc. 2010, 133, 1209
23. Galloway, W. R. J. D.; Isidro-Llobet, A.; Spring, D. R. Nature Commun. 2010, 1, 80
24. Eberhadt, L.; Kumar, K.; Waldmann, H. Curr. Drug Targets 2011, 12, 1531
25. Wei, H.; Yin, L.; Luo, H.; Li, X.; Chan, A. S. C. Chirality 2011, 23, 222
26. The use of this ligand in the formation of diaryl ethers has previously been reported. See, for example: Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623