An efficient synthesis of 2-trifluoromethyl quinolines via gold-catalyzed cyclization of trifluoromethylated propargylamines

Journal of Fluorine Chemistry

Volumn 135, Issue , 2012, Pages 195-199

  Zhu, Mei ^a   Fu, Weijun ^a   Zou, Guanglong ^b   Xun, Chen ^a   Deng, Dongsheng ^a   Ji, Baoming ^a  

^a LUOYANG NORMAL UNIVERSITY   (China)

^b GUIZHOU UNIVERSITY   (China)

Author keywords

Cyclization; Gold; Propargylamine; Quinoline

Indexed keywords

EID: 84857369787     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2011.11.002     Document Type: Article

References (57)

1. V.V. Kouznetsov, L.Y. Vargas Méndez, and C.M. Meléndez Gómez Curr. Org. Chem. 9 2005 141 161
2. J.P. Michael Nat. Prod. Rep. 14 1997 605 618
3. M. Balasubramanian, and J.G. Keay A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II 1996 Pergamon Press Oxford 245 265
4. I.L. Baraznenok, V.G. Nenajdenko, and E.S. Balenkova Eur. J. Org. Chem. 4 1999 937 941
5. B. Crousse, J.P. Bégué, and D. Bonnet-Delpon J. Org. Chem. 65 2000 5009 5013
6. J. Takaya, H. Kagoshima, and T. Akiyama Org. Lett. 2 2000 1577 1579
7. T. Fuchigami, and S. Ichikawa J. Org. Chem. 59 1994 607 615
8. M. Schlosser, H. Keller, S.Sumida, and J. Yang Tetrahedron Lett. 38 1997 8523 8526
9. E.J. Latham, S.M. Murphy, and S.P. Stanfoth Tetrahedron Lett. 35 1994 3395 3396
10. L. Strekowski, S.Y. Lin, H. Lee, Z.Q. Zhang, and J.C. Mason Tetrahedron 54 1998 7947 7954
11. H. Xie, J. Zhu, Z. Chen, S. Li, and Y. Wu Synlett 2010 2659 2663
12. L. Strekowski, A. Czarny, and H. Lee J. Fluorine Chem. 104 2000 281 284
13. C.J. Ohnmacht, A.R. Patel, and R.E. Lutz J. Med. Chem. 14 1971 926 928
14. H.J. Dyke, J.G. Montana, WO 2000026208, 2000.
15. R. Kuang, D. Blythin, N.Y. Shih, H.J. Shue, X. Chen, J. Cao, D. Gu, Y. Huang, J.H. Schwerdt, P.C. Ting, S.C. Wong, L. Xiao, WO 2005116009, 2005.
16. J.L. Mao, B.J. Wan, Y.H. Wang, S.G. Franzblau, and A.P. Kozikowski ChemMedChem 2 2007 811 813
17. A. Lilienkampf, J.L. Mao, B.J. Wan, Y.H. Wang, S.G. Franzblau, and A.P. Kozikowski J. Med. Chem. 52 2009 2109 2118
18. H. Sakashita, T. Yoshida, H. Kitajima, M. Takeuchi, Y. Tanaka, T. Yoshimura, F. Akahoshi, Y. Hayashi, WO 2003024942, 2003.
19. J. Dade, O. Provot, H. Moskowitz, J. Mayrargue, and E. Prina Chem. Pharm. Bull. 49 2001 480 483
20. J.B. Dickey, J.G. McNally, US Patent 2432393, 1947.
21. M.S. Raasch J. Org. Chem. 27 1962 1406 1409
22. Y. Kobayashi, and I. Kumadaki Tetrahedron Lett. 10 1969 4095 4096
23. H. Amii, Y. Kishikawa, and K. Uneyama Org. Lett. 3 2001 1109 1112
24. S. Li, Y. Yuan, J. Zhu, H. Xie, Z. Chen, and Y. Wu Adv. Synth. Catal. 352 2010 1582 1586
25. L. Zhang, J. Sun, and S.A. Kozmin Adv. Synth. Catal. 348 2006 2271 2296
26. A. Furstner, and P.W. Davies Angew. Chem. Int. Ed. 46 2007 3410 3449
27. E. Jimenez-Nunez, and A.M. Echavarren Chem. Commun. 33 2007 3 346
28. D.J. Gorin, and F.D. Toste Nature 446 2007 395 403
29. A.S.K. Hashmi Chem. Rev. 107 2007 3180 3211
30. N. Marion, and S.P. Nolan Angew. Chem. Int. Ed. 46 2007 2750 2752
31. A.S.K. Hashmi Nature 449 2007 292 293
32. G. Dyker Angew. Chem. Int. Ed. 39 2000 4237 4239
33. R.C.D. Brown Angew. Chem. Int. Ed. 44 2005 850 852
34. A.S.K. Hashmi Angew. Chem. Int. Ed. 44 2005 6990 6993
35. S. Ma, S. Yu, and Z. Gu Angew. Chem. Int. Ed. 45 2006 200 203
36. Z.J. Li, C. Brouwer, and C. He Chem. Rev. 108 2008 3239 3265
37. N.T. Patil, and Y. Yamamoto ARKIVOC 5 2007 6 19
38. A.S.K. Hashmi, and G.J. Hutchings Angew. Chem. Int. Ed. 45 2006 7896 7936
39. J. Barluenga, A. Dieguez, A. Fernandez, F. Rodriguez, and F.J. Fananas Angew. Chem. Int. Ed. 45 2006 2091 2093
40. A. Buzas, and F. Gagosz Synlett 2006 2727 2730
41. A.S.K. Hashmi, R. Salathe, and W. Frey Synlett 2007 1763 1766
42. P. Dube, and F.D. Toste J. Am. Chem. Soc. 128 2006 12062 12063
43. S. Hotha, and S. Kashyap J. Am. Chem. Soc. 128 2006 9620 9621
44. B. Gockel, and N. Krause Org. Lett. 8 2006 4485 4488
45. D.J. Gorin, N.R. Davis, and F.D. Toste J. Am. Chem. Soc. 127 2005 11260 11261
46. C. Brouwer, R. Rahaman, and C. He Synlett 2007 1785 1789
47. I. Nakamura, T. Sato, and Y. Yamamoto Angew. Chem Int. Ed. 45 2006 4473 4475
48. I. Nakamura, T. Sato, M. Terada, and Y. Yamamoto Org. Lett. 9 2007 4081 4083
49. J. Sun, M.P. Conley, L.Zhang, and S.A. Kozmin J. Am. Chem. Soc. 128 2006 9705 9710
50. V. Mamane, P. Hannen, and A. Fürstner Chem. Eur. J. 10 2004 4556 4575
51. C. Nevado, and A.M. Echavarren Chem. Eur. J. 11 2005 3155 3164
52. M.T. Reetz, and K. Sommer Eur. J. Org. Chem. 2003 3485 3496
53. X. Huang, and W. Fu Tetrahedron Lett. 49 2008 2359 2362
54. W. Fu, C. Xu, G. Zou, D. Hong, D. Deng, Z. Wang, and B. Ji Synlett 2009 763 766
55. W. Fu, G. Zou, M. Zhu, D. Hong, D. Deng, C. Xun, and B. Ji J. Fluor. Chem. 130 2009 996 1000
56. K. Uneyama, and H. Watanabe Tetrahedron Lett. 32 1991 1459 1462
57. P.R. Likhar, M.S. Subhas, S. Roy, M.L. Kantam, B. Sridhar, R.K. Seth, and S. Biswas Org. Biomol. Chem. 7 2009 85 93