A new route to tricyclic 2-pyridone frameworks via formation of bicyclic N-alkenyl alkynylamides followed by gold-catalyzed cycloisomerization

Chemistry Letters

Volumn 38, Issue 12, 2009, Pages 1152-1153

  Imase, Hidetomo ^a   Tanaka, Ken ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449148716     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.1152     Document Type: Article

References (35)

1. For recent reviews, see: a) M. Torres, S. Oil, M. Parra, Curr. Org. Chem. 2005, 9, 1757.
2. b) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127.
3. c) J. H. Rigby, Synlett 2000, 1.
4. a) K. Tanaka, A. Wada, K. Nogucbi, Org. Lett. 2005, 7, 4737.
5. b) Y. Yamamoto, K. Kinpara, T. Saigoku, H. Takagishi, S. Okuda, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2005, 127, 605.
6. c) H. A. Duong, M. J. Cross, J. Louie, J. Am. Chem. Soc. 2004, 126, 11438.
7. d) L. V. R. Bonaga, H.-C. Zhang, D. A. Gauthier, I. Reddy, B. E. Maryanoff, Org. Lett. 2003, 5, 4537.
8. e) T. Takahashi, F.-Y. Tsai, Y. Li, H. Wang, Y. Kondo, M. Yamanaka, K. Nakajima, M. Kotora, J. Am. Chem. Soc. 2002, 124, 5059, and references therein.
9. R. A. Earl, K. P. C. Vollhardt, J. Org. Chem. 1984, 49, 4786.
10. For recent reviews of synthesis of azaheterocycles including 2-pyridones by transition metal mediated [2 + 2 + 2] cycloadditions, see: a) B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085.
11. b) P. R. Chopade, J. Louie, Adv. Synth. Catal. 2006, 348, 2307.
12. c) J. A. Varela, C. Saà, Chem. Rev. 2003, 103, 3787.
13. a) H. Imase, K. Noguchi, M. Hirano, K. Tanaka, Org. Lett. 2008, 10, 3563.
14. b) H. Imase, T. Suda, Y. Shibata, K. Noguchi, M. Hirano, K. Tanaka, Org. Lett. 2009, 11, 1805.
15. For selected recent examples of cycloisomerizations of 1,5-enynes to form six-membered compounds, see: a) J. Sun, M. P. Conley, L. Zhang, S. A. Kozmin, J. Am. Chem, Soc. 2006, 128, 9705.
16. b) B. D. Sherry, L. Maus, B. N. Laforteza, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 8132.
17. c) M. Movassaghi, M. D. Hill, J. Am. Chem, Soc. 2006, 128, 4592.
18. d) T. Shibata, Y. Ueno, K. Kanda, Synlett 2006, 411.
19. e) C. Nieto-Oberhuber, M. P. Muñoz, S. López, E. Jiménez-Núñez, C. Nevado, E. Herrero-Gómez, M. Raducan, A. M. Echavarren, Chem.-Eur. J. 2006, 12, 1677.
20. f) C. M. Grisé, L. Barriault, Org. Lett. 2006, 8, 5905.
21. g) S. Datta, A. Odedra, R.-S. Liu, J. Am. Chem. Soc. 2005, 127, 11606.
22. h) C. Fehr, J. Galindo, Angew. Chem., Int. Ed. 2006, 45, 2901.
23. i) H. Imagawa, T. Iyenaga, M. Nishizawa, Org. Lett. 2005, 7, 451.
24. j) V. Mamane, P. Hannen, A. Fürstner, Chem.-Eur. J. 2004, 10, 4556, and references therein.
25. For recent reviews of cycloisomerizations of 1,n-enynes, see: a) V. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem., Int. Ed. 2008, 47, 4268.
26. b) L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271.
27. c) C. Bruneau, Angew. Chem., Int. Ed. 2005, 44, 2328.
28. d) L. Añorbe, G. Domínguez, J. Pérez-Castells, Chem. - Eur. J. 2004, 10, 4938.
29. a) A. Padwa, A. C. Flick, H. Lee, Org. Lett. 2005, 7, 2925.
30. b) A. Padwa, S. R. Hairing, M. A. Semones, J. Org. Chem. 1998, 63, 44.
31. c) C. H. Heathcock, M. H. Norman, D. A. Dickman, J. Org. Chem. 1990, 55, 798.
32. d) D. A. Dickman, C. H. Heathcock, J. Am. Chem. Soc. 1989, 111, 1528.
33. Supporting Information, is available electronically on the CSJ-Joumal Web site, http://www.csj.jp/journals/chem-lett/index.html.
34. B. J. Neubert, B. B. Snider, Org. Lett. 2003, 5, 765.
35. H. O. House, W. L. Roelofs, B. M. Trost, J. Org. Chem. 1966, 31, 646.