Sulfur-assisted and 1,8-diazabicy clo [5.4.0] undec-7-ene (DBU)catalyzed cyclization of 2-alkynylanilines for the metal-free synthesis of indole derivatives

Advanced Synthesis and Catalysis

Volumn 352, Issue 13, 2010, Pages 2127-2131

  Zhou, Hongwei ^a   Zhu, Da ^a   Xing, Yanpeng ^a   Huang, Huafeng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

1,8 diazabicyclo 5.4.0 undec 7 ene (DBU); Cyclization; DBU catalyzed reaction; Indole derivatives; Metal free conditions; Sulfur assisted recation

Indexed keywords

EID: 77956931324     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000280     Document Type: Article

References (50)

1. For reviews, please see: a) M. Somei, F. Yamada, Nat. Prod. Rep. 2004, 27, 278-311;
2. b) M. Lounasmaa, A. Tolvanen, Nat. Prod. Rep. 2000, 17, 175-191;
3. J. A. Joule, in: Science of Synthesis (Houben-Weyl Methods of Molecular Transformations), (Ed. : E. J. Thomas), Georg Thieme Verlag, Stuttgart, 2000, Vol. 10, pp 361-652;
4. J. E. Saxton, Nat. Prod. Rep. 1997, 14, 559-590;
5. e) B. Robinson, Chem. Rev. 1963, 63, 370-401.
6. a) K. Alex, A. Tillack, N. Schwarz, M. Beller, Angew. Chem. 2008, 120, 2337-2340;
7. Angew. Chem. Int. Ed. 2008, 47, 2304-2307;
8. b) S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 10251-10263.
9. a) G. T. Li, X. G. Huang, L. M. Zhang, Angew. Chem. 2008, 120, 352-355;
10. Angew. Chem. Int. Ed. 2008, 47, 346-349;
11. b) B. M. Trost, A. McClory, Angew. Chem. 2007, 119, 2120-2123;
12. Angew. Chem. Int. Ed. 2007, 46, 2074-2077;
13. H. Ohno, Y. Ohta, S. Oishi, N. Fujii, Angew. Chem. 2007, 119, 2345-2348;
14. Angew. Chem. Int. Ed. 2007, 46, 2295-2298;
15. K. Cariou, B. Ronan, S. Mignani, L. Fensterbank, M. Malacria, Angew. Chem. 2007, 119, 1913-1916;
16. Angew. Chem. Int. Ed. 2007, 46, 1881-1884;
17. e) I. Nakamura, U. Yamagishi, D. Song, S. Konta, Y. Yamamoto, Angew. Chem. 2007, 779, 2334-2337;
18. Angew. Chem. Int. Ed. 2007, 46, 2284-2287;
19. f) H. A. Oskooie, M. M. Heravi, F. K. Behbahani, Molecules 2007, 12, 1438-1446;
20. g) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, L. M. Parisi, J. Org. Chem. 2005, 70, 6213-6217.
21. a) J. Barluenga, A. Jimenez-Aquino, F. Aznar, C. Valdes, J. Am. Chem. Soc. 2009, 131, 4031-4041;
22. b) K. Okuma, J. I. Seto, K. I. Sakaguchi, S. Ozaki, N. Nagahora, K. Shioji, Tetrahedron Lett. 2009, 50, 2943-2945;
23. Y. Chen, Y. J. Wang, Z. M. Sun, D. W. Ma, Org. Lett. 2008, 10, 625-628;
24. T. Jensen, H. Pedersen, B. BangAndersen, R. Madsen, M. Jørgensen, Angew. Chem. 2008, 120, 902-904;
25. Angew. Chem. Int. Ed. 2008, 47, 888-890;
26. e) O. Leogane, H. Lebel, Angew. Chem. 2008, 220, 356-358;
27. Angew. Chem. Int. Ed. 2008, 47, 350-352;
28. f) J. Barluenga, A. Jimenez-Aquino, C. Valdes, F. Aznar, Angew. Chem. 2007, 119, 1551-1554;
29. Angew. Chem. Int. Ed. 2007, 46, 1529-1532;
30. g) A. Fayol, Y. Q. Fang, M. Lautens, Org. Lett. 2006, 8, 4203-4206;
31. h) J. R. Dunetz, R. L. Danheiser, J. Am. Chem. Soc. 2005, 127, 5776-5777;
32. C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003,125, 4054-4055.
33. B. J. Stokes, H. J. Dong, B. E. Leslie, A. L. Pumphrey, T. G. Driver, J. Am. Chem. Soc. 2007, 129, 7500-7501.
34. 2O, chromatography on silica gel (eluent: EtOAc/petroleum ether = 1:15) of the crude product afforded la in a yield of 92%.
35. a) A. H. Stoll, P. Knochel, Org. Lett. 2008, 10, 113-116;
36. b) J. Wang, N. Soundarajan, N. Liu, K. Zimmermann, B. N. Naidu, Tetrahedron Lett. 2005, 46, 907-910;
37. C. Koradin, W. Dohle, A. L. Rodriguez, B. Schmid, P. Knochel, Tetrahedron 2003, 59, 1571-1587;
38. A. L. Rodriguez, C. Koradin, W. Dohle, P. Knochel, Angew. Chem. 2000, 112, 2607-2609;
39. Angew. Chem. Int. Ed. 2000, 39, 2488-2490;
40. e) Y. Kondo, S. Kojima, T. Sakamoto, J. Org. Chem. 1997, 62, 6507-6511.
41. a) H. Zhou, D. Zhu, Y. Xie, H. Huang, K. Wang, J. Org. Chem. 2010, 75, 2706;
42. b) H. Zhou, Y. Xie, L. Ren, R. Su, Org. Lett. 2010, 12, 356-359.
43. a) Z. Yu, J. G. Verkade, Tetrahedron Lett. 1998, 39, 2671-2674;
44. b) C. G. Gutierrez, L. R. Summerhays, J. Org. Chem. 1984, 49, 5206-5213.
45. a) S. Nakamura, R. Nakagawa, Y. Watanabe, T. Toru, J. Am. Chem. Soc. 2000, 122, 11340-11347;
46. b) E.A. Castro, R. Cortes, J. G. Santos, J. C. Vega, J. Org. Chem. 1982, 47, 3774-3777.
47. a) B. L. Soltz, J. Y. Corey, J. Organomet. Chem. 1979, 171, 291-299;
48. b) J. F. Biellman, J.B. Ducep, Tetrahedron Lett. 1968, 9, 5605-5714.
49. a) Y. Arroyo, J. F. Rodríguez, M. Santos, M. A. S. Tejedor, J. L. G. Ruano, J. Org. Chem. 2007, 72,1035-1038;
50. b) T. Harada, M. Morimoto, M. Nagasawa, N. Takamura, H. Inoue, T. Ohishi, M. Takeda, Chem. Pharm. Bull. 1992, 40, 1986-1989.