Copper(I)- And gold(I)-catalyzed synthesis of 2,4-disubstituted quinoline derivatives from N-Aryl-2-propynylamines

Chemistry Letters

Volumn 36, Issue 12, 2007, Pages 1422-1423

  Kuninobu, Yoichiro ^a   Inoue, Yuichi ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38149123939     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1422     Document Type: Article

References (32)

1. a) C. W. Tang, S. A. Van Slyke, Appl. Phys. Lett. 1987, 51, 913.
2. b) J. I. Kim, I. S. Shin, H. Kim, J.-K. Lee, J. Am. Chem. Soc 2005, 127, 1614.
3. a) J. S. Sawyer, B. D. Anderson, D. W. Beight, R. M. Campbell, M. L. Jones, D. K. Herron, J. W. Lampe, J. R. McCowan, W. T. McMillen, N. Mort, S. Parsons, E. C. R. Smith, M. Vieth, L. C. Weir, L. Yan, F. Zhang, J. M. Yingling, J. Med. Chem. 2003, 46, 3953.
4. b) J. Singh, C. E. Chuaqui, P. Ann Boriack-Sjodin, W.-C. Lee, T. Pontz, M. J. Corbley, H.-K. Cheung, R. M. Arduini, J. N. Mead, M. N. Newman, J. L. Papadatos, S. Bowes, S. Josiah, L. E. Ling, Bioorg. Med. Chem. Lett. 2003, 13, 4355.
5. c) P. G. Bray, S. A. Ward, P. M. O'Neill, Curr. Top. Microbiol. 2005, 295, 3.
6. F. Tiemann, J. Oppermann, Ber. Dtsch. Chem. Ges. 1880, 13, 2056.
7. O. Doebner, W. von Miller, Ber. Dtsch. Chem. Ges. 1881, 14, 2812.
8. A. Combes, Bull Soc. Chim. Fr. 1883, 49, 89.
9. G. L. Ciamician, M. Dennstedt, Ber. Dtsch. Chem. Ges. 1881, 14, 1153.
10. X. Zhang, M. A. Campo, T. Yao, R. C. Larock, Org. Lett. 2005, 7, 763.
11. For a zinc(II)-mediated reaction, see: B. Jiang, Y.-G. Si, J. Org. Chem. 2002, 67, 9449.
12. a) M. Beller, O. R. Thiel, H. Trauthwein, C. G. Hartung, Chem.-Eur. J. 2000, 6, 2513.
13. b) H. Z. Syeda Huma, R. Haider, S. S. Kalra, J. Das, J. Iqbal, Tetrahedron Lett. 2002, 43, 6485.
14. c) J. Jacob, W. D. Jones, J. Org. Chem. 2003, 68, 3563.
15. d) D. K. O'Dell, K. M. Nicholas, J. Org. Chem. 2003, 68, 6427.
16. e) G. Abbiati, A. Arcadi, F. Marinelli, E. Rossi, M. Verdecchia, Synlett 2006, 3218.
17. f) R. P. Korivi, C.-H. Cheng, J. Org. Chem. 2006, 71, 7079.
18. g) T. Nakajima, T. Inada, T. Igarashi, T. Sekioka, I. Shimizu, Bull. Chem. Soc. Jpn. 2006, 79, 1941.
19. h) A. W. Sromek, A. L. Rheingold, D. J. Wink, V. Gevorgyan, Synlett 2006, 2325.
20. i) M. Movassaghi, M. D. Hill, J. Am. Chem. Soc. 2006, 128, 4592.
21. 2, 39%.
22. Copper-catalyzed synthesis of quinoline derivatives has already been reported. However, the yield of quinolines and efficiency were low. See: ref. 9b.
23. In this reaction, 1,2-dihydroquinoline was not detected.
24. Results for other acceptors are as follows: norbornene, 39%; 3,3-dimethyl-1 -butene, 46%; 3-pentanone, 18%; acetophenone, 43%; nonanal, 58%; benzaldehyde, 59%.
25. 2 was used as an oxidant, the yield of 2a could not be improved.
26. Benzylphenylamine was obtained in 91% yield.
27. Only a trace amount of quinoline 2f was formed in the absence of AgOTf.
28. There have been some reports on copper(I)-catalyzed synthesis of 2-propynylamines from aldimines and terminal acetylenes. See: a) C. Wei, C-J. Li, J. Am. Chem. Soc. 2002, 124, 5638.
29. b) J. N. Rosa, A. Gil Santos, C. A. M. Afonso, J. Mol. Catai. A: Chem. 2004, 214, 161.
30. c) M. Benaglia, D. Negri, G. Dell'Anna, Tetrahedron Lett. 2004, 45, 8705.
31. 3, 91%.
32. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.