Copper(I)-catalyzed synthesis of novel 4-(trifluoromethyl)-[1,2,3] triazolo[1,5-a]quinoxalines via cascade reactions of N-(o-haloaryl)alkynylimine with sodium azide

Advanced Synthesis and Catalysis

Volumn 352, Issue 8, 2010, Pages 1296-1300

  Chen, Zixian ^a,b   Zhu, Jiangtao ^b   Xie, Haibo ^b   Li, Shan ^b   Wu, Yongming ^b   Gong, Yuefa ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

C N cross coupling; Cascade reactions; Copper; Quinoxalines; Trifluoromethyl substituents

Indexed keywords

EID: 77952708583     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.200900875     Document Type: Article

References (45)

1. a) H. C. Shen, F. Ding, Q. Deng, L. C. Wilsie, M. L. Krsmanovic, A. K. Taggart, E. Carballo-Jane, N. Ren, T. Cai, T. Wu, K. K. Wu, K. Cheng, Q. Chen, M. S. Wolff, X. Tong, T. G. Holt, M. G. Waters, M. L. Hammond, J. R. Tata, S. L. Colletti, J. Med. Chem. 2009, 52, 2587-2602;
2. b) A. Lauria, C. Patella, G. Dattolo, A. M. Almerico, J. Med. Chem. 2008, 57, 2037-2046;
3. c) F. Da Settimo, G. Primofiore, S. Taliani, A. M. Marini, C. La Motta, F. Simorini, S. Salerno, V. Sergianni, T. Tuccinardi, A. Martinelli, B. Cosimelli, G. Greco, E. Novellino, O. Ciampi, M. L. Trincavelli, C. Martini, J. Med. Chem. 2007, 50, 5676-5684;
4. d) G. Biagi, I. Giorgi, O. Livi, V. Scartoni, L. Betti, G. Giannaccini, M. L. Trincavelli, Eur. J. Med. Chem. 2002, 37, 565-571;
5. e)A. W Thomas, Bioorg. Med. Chem. Lett. 2002, 12, 1881-1884;
6. f) L. Bertelli, G. Biagi, I. Giorgi, C. Manera, O. Livi, V. Scartoni, L. Betti, G. Giannaccini, L. Trincavelli, P. L. Barili, Eur. J. Med. Chem. 1998, 33, 113-122;
7. g) L. Betti, G. Biagi, G. Giannaccini, I. Giorgi, O. Livi, A. Lucacchini, C. Manera, V. Scartoni, J. Med. Chem. 1998, 41, 668-673;
8. h) J. L. Kelley, C. S. Koble, R. G. Davis, E. W. McLean, F. E. Soroko, B. R. Cooper, J. Med. Chem. 1995, 38, 4131-4134;
9. i) I. R. Ager, A. C. Barnes, G. W Danswan, P. W. Hairsine, D. P. Kay, P. D. Kennewell, S. S. Matharu, P. Miller, P. Robson, J. Med. Chem. 1988, 31, 1098-1115;
10. j) E. J. Trybulski, L. Benjamin, S. Vitone, A. Walser, R. I. Fryer, J. Med. Chem. 1983, 26, 367-372.
11. I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, 2009.
12. B. Saha, S. Sharma, D. Sawant, B. Kundu, Tetrahedron 2008, 64, 8676-8684.
13. For copper-catalyzed C-N bond formation reactions, see: a) D. W. Ma, Y. D. Zhang, J. C. Yao, S. H. Wu, F. G. Tao, J. Am. Chem. Soc. 1998, 720, 12459-12467;
14. b) A. Klapars, X. H. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 7421-7428;
15. c) J. C. Antilla, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 11684-11688;
16. d) F. Y. Kwong, A. Klapars, S. L. Buchwald, Org. Lett. 2002, 4, 581-584;
17. e) D. W. Ma, Q. Cai, H. Zhang, Org. Lett. 2003, 5, 2453-2455;
18. f) H. J. Cristau, P. P. Cellier, J. F. Spindler, M. Taillefer, Chem. Eur. J. 2004, 10, 5607-5622;
19. g) H. H. Rao, H. Fu, Y. Y. Jiang, Y. F. Zhao, J. Org. Chem. 2005, 70, 8107-8109;
20. h) H. Zhang, Q. Cai, D.W. Ma, J. Org. Chem. 2005, 70, 5164-5173;
21. i) Z. Lu, R. J. Twieg, Tetrahedron Lett. 2005, 46, 2997-3001;
22. j) A. Shafir, S. L. Buchwald, J. Am. Chem. Soc. 2006, 128, 8742-8743;
23. k) B. De Lange, M. H. Lambers-Verstappen, L. Schmieder-van de Vondervoort, N. Sereinig, R. de Rijk, A. de Vries, Synlett 2006, 3105-3109;
24. l) L. Rout, S. Jammi, T. Punniyamurthy, Org. Lett. 2007, 9, 3397-3399;
25. m) R. A. Altman, E. D. Koval, S. L. Buchwald, J. Org. Chem. 2007, 72, 6190-6199;
26. n) R. A. Altman, A. Shafir, A. Choi, P. A. Lichtor, S. L. Buchwald, J. Org. Chem. 2008, 73, 284-286.
27. For cascade processes involving a copper-catalyzed C-N coupling reaction, see: a) X. Y. Yuan, X. B. Xu, X. B. Zhou, J. W. Yuan, L. G. Mai, Y. Z. Li, J. Org. Chem. 2007, 72, 1510-1513;
28. b)C. P. Jones, K. W. Anderson, S. L. Buchwald, J. Org. Chem. 2007, 72, 7968-7973;
29. c) B. L. Zou, O. L. Yuan, D. W. Ma, Org. Lett. 2007, 9, 4291-4294;
30. d) B. L. Zou, Q. L. Yuan, D. W. Ma, Angew. Chem. 2007, 119, 2652-2655;
31. Angew. Chem. Int. Ed.2007, 46, 2598-2601;
32. e)F. S. Melkonyan, A. V. Karchava, M. A. Yurovskaya, J. Org. Chem. 2008, 73, 4275-4278;
33. f) D. S. Yang, H. Fu, L. M. Hu, Y. Y. Jiang, Y. F. Zhao, J. Org. Chem. 2008, 73, 7841-7844;
34. g) K. Hasegawa, N. Kimura, S. Arai, A. Nishida, J. Org. Chem. 2008, 73, 6363-6368;
35. h) A. Minatti, S. L. Buchwald, Org. Lett. 2008, 10, 2721-2724;
36. i) L. Guo, B. Li, W. L. Huang, G. Pei, D.W. Ma, Synlett 2008, 1833-1836;
37. j) J.T Zhu, H. B. Xie, Z. X. Chen, S. Li, Y. M. Wu, Chem. Commun. 2009, 2338-2340.
38. Y. Tanaka, S. R. Velen, S. I. Miller, Tetrahedron 1973, 29, 3271-3283.
39. CCDC 755240 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
40. Fluorine-containing N-(o-haloaryl)alkynylimines were synthesized using a new method created by our group recently (in press), which is detailed in the Supporting Information.
41. For copper-catalyzed C-N bond formation with aryl chlorides, see: a) A. Klapars, X. H. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 7421-7428;
42. b) S. U. Son, I. K. Park, J. Park, T. Hyeon, Chem. Commun. 2004, 778-779;
43. c) H. C Ma, X. Z. Jiang, J. Org. Chem. 2007, 72, 8943-8946;
44. d) H.H. Xu, C. Wolf, Chem. Commun. 2009, 1715-1717;
45. e) H. H. Xu, C. Wolf, Chem. Commun. 2009, 3035-3037.