Gold(I)-catalyzed cascade for synthesis of pyrrolo[1,2-a:2′,1′- c]-/ pyrido[2,1-c]pyrrolo[1,2-a]quinoxalinones

Advanced Synthesis and Catalysis

Volumn 352, Issue 10, 2010, Pages 1711-1717

  Zhou, Yu ^a   Ji, Xun ^a,b   Liu, Guannan ^a   Zhang, Dengyou ^a   Zhao, Linxiang ^b   Jiang, Hualiang ^a   Liu, Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Alkynes; Aromatic amines; Cascade reactions; Gold catalysts; Pyrrolo 1,2 a:2 ,1 c pyrido 2,1 c pyrrolo 1,2 a quinoxalinones

Indexed keywords

EID: 77954794962     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000199     Document Type: Article

References (41)

1. For recent reviews, see : a) A. K. Verma, T. Kesharwani, J. Singh, V. Tandon, R. C. Larock, Angew. Chem. 2009, 121, 1158;
2. Angew. Chem. Int. Ed. 2009, 48, 1138;
3. b) X.-Y Liu, C.-M. Che, Angew. Chem. 2008, 120, 3865;
4. Angew. Chem. Int. Ed. 2008, 47, 3805;
5. c) J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001;
6. d) A. de Meijere, P. Von Zezschwitz, S. BrIse, Acc.. Chem. Res. 2005, 38, 413;
7. e) J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302;
8. f) A. Ajamian, J. L. Gleason, Angew. Chem. 2004, 116, 3842;
9. Angew. Chem. Int. Ed. 2004, 43, 3754.
10. a) T. Yang, L. Campbell, D. J. Dixon, J. Am. Chem. Soc. 2007, 129, 12070;
11. b) D. J. Gorin, F.D. Toste, Nature 2007, 446, 395;
12. c) A. S. K. Hashmi, Catal. Today 2007, 122, 211;
13. d) A. S. K. Hashmi, G.J. Hutchings, Angew. Chem. 2006, 118, 8064;
14. Angew. Chem. Int. Ed. 2006, 45, 7896;
15. e) A. S. K. Hashmi, Angew. Chem. Int. Ed. 2005, 44, 6690;
16. f) A. S. K. Hashmi, Gold Bull. 2004, 37, 51.
17. a) Y. Zhou, Y. Zhai, X. Ji, G. Liu, E. Feng, D. Ye, L. Zhao, H. Jiang, H. Liu, Adv. Synth. Catal. 2010, 352, 373;
18. b) D. Ye, X. Zhang, Y. Zhou, D. Zhang, L. Zhang, H. Wang, H. Jiang, H. Liu, Adv. Synth. Catal. 2009, 357, 2770;
19. c) Y. Zhou, E. Feng, G. Liu, D. Ye, J. Li, H. Jiang, H. Liu, J. Org. Chem. 2009, 74, 7344;
20. d) G. Liu, Y. Zhou, D. Ye, D. Zhang, X. Ding, H. Jiang, H. Liu, Adv. Synth. Catal. 2009, 351, 2605;
21. e) D. Ye, J. Wang, X. Zhang, Y. Zhou, X. Ding, E. Feng, H. Sun, G. Liu, H. Jiang, H. Liu, Green Chem. 2009, 11, 1201;
22. f) H. Huang, H. Jiang, K. Chen, H. Liu, J. Org. Chem. 2009, 74, 5476;
23. g) E. Feng, H. Huang, Y. Zhou, D. Ye, H. Jiang, H. Liu, J. Org. Chem. 2009, 74, 2846;
24. h) Z. Li, H. Sun, H. Jiang, H. Liu, Org. Lett. 2008, 10, 3263.
25. For selected examples, see: a) Y. Murata, D. Yamashita, K. Kitahara, Y. Minasako, A. Nakazaki, S. Kobayashi, Angew. Chem. 2009, 121, 1428;
26. b) A Dieguez-Vazquez, C. C. Tzschucke, W. Y. Lam, S. V. Ley, Angew. Chem. 2008, 120, 216;
27. c) H. Li, T. P. Loh, J. Am. Chem. Soc. 2008, 130, 7194;
28. d) R. Felstead, S. E. Gibson, A. Rooney, E. S. Y. Tse, Eur. J. Org. Chem. 2008, 4963;
29. e) M. R. Axet, J. B. Buchholz, C Claver, S. Castillon, Adv. Synth. Catal. 2007, 349, 1983;
30. f) D. Enders, M. R. M. Huttl, C. Grondai, G. Raabe, Nature 2006, 441, 861.
31. a) C. I. HerrerTas, X. Yao, Z. Li, C.-J. Li, Chem. Rev. 2007, 107, 2546;
32. b) U.M. Lindström, F. Andersson, Angew. Chem. 2006, 118, 562;
33. Different substituted 2-(1H-pyrrol-1-yl)anilines were synthesized by using substituted-2-fluoronitrobenzene and the corresponding amines as the starting materials via modified procedures reported by the Agarwal group and the Moarbess group: a) P. K. Agarwal, D. Sawant, S. Sharma, B. Kundu, Eur. J. Org. Chem. 2009, 292;
34. b) G. Moarbess, C. Deleuze-Masquefa, V. Bonnard, S. Gayraud-Paniagua, J. R. Vidal, F. Bressolle, F. Pinguet, P. A. Bonnet, Bioorg. Med. Chem. 2008, 16, 6601.
35. CCDC 761511 contains the supplementary crystallographic data for 3La.These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
36. a) A. S. K. Hashmi, R. Salathé, W. Frey, Eur. J. Org. Chem. 2007, 1648;
37. b) A. Arcadi, S. Di Giuseppe, F. Marinelli, E. Rossi, Adv. Synth. Catal. 2001, 343, 443;
38. (c) A. Arcadi, G. Bianchi, S. Di Guiseppe, F. Marinelli, Green Chem. 2003, 5, 64.
39. a) E. Genin, P. Y. Toullec, S. Antoniotti, C. Brancour, J.-P. Genet, V. Michelet, J. Am. Chem. Soc. 2006, 128, 3112;
40. b) H. Harkat, J. M. Weibel, P. Pale, Tetrahedron Lett. 2006, 47, 6273.
41. 1 catalyst (2 mol%). After stirring for 10 min at room temperature, 2-(1H-pyrrol-1-yl)aniline (0.5 mmol) and TFA (10mol%) were added. Subsequently, the reaction vial was sealed and the mixture was heated to 80°C for 2 h. And then, the cold mixture was concentrated under reduced pressure, the resulting reside was purified by flash column chromatography (petroleum ether/ethyl acetate = 5/1, v/v, as an eluent) to afford 3Aa; yield: 97%. (Figure Presented)