One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling

Organic Letters

Volumn 7, Issue 20, 2005, Pages 4487-4489

  Mohamed Ahmed, Mohamed S ^a   Kobayashi, Kei ^a   Mori, Atsunori ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRALAZINE; ISOXAZOLE DERIVATIVE; PALLADIUM; PYRAZOLE; PYRAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; HYDRALAZINE; ISOXAZOLES; MOLECULAR STRUCTURE; PALLADIUM; PYRAZOLES;

EID: 26444497881     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051841j     Document Type: Article

References (26)

1. (a) Zificsak, C. A.; Hlasta, D. J. Tetrahedron 2004, 60, 8991.
2. (b) Haino, T.; Tanaka, M.; Ikeda, K.; Kubo, K.; Mori, A.; Fukazawa, Y. Tetrahedron Lett. 2004, 45, 2277.
3. (a) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
4. (b) Masui, K.; Ikegami, H.; Mori, A. J. Am. Chem. Soc. 2004, 126, 5074.
5. (c) Masui, K.; Mori, A.; Okano, K.; Takamura, K.; Kinoshita, M.; Ikeda, T. Org. Lett. 2004, 6, 2011.
6. An example of recent multicomponent construction of ring structures with a transition metal catalyst: (a) Yamamoto, Y.; Ishii, J.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2004, 126, 3712.
7. (b) Krazinski, A.; Radic, Z.; Manetsch, R.; Raushel, J.; Taylor, P.; Sharpless, K. B.; Kolb, H. C. J. Am. Chem. Soc. 2005, 127, 6686.
8. (a) Mohamed Ahmed, M. S.; Mori, A. Org. Lett. 2003, 5, 3057.
9. (b) Mohamed Ahmed, M. S.; Sekiguchi, A.; Masui, K.; Mori, A. Bull. Chem. Soc. Jpn. 2005, 78, 160.
10. (a) Claisen, L. Ber. Dtsch. Chem. Ges. 1903, 36, 3664.
11. (b) Engelmann, A.; Kirmse, W. Chem. Ber. 1973, 106, 3092.
12. (c) Grotjahn, D. B.; Van, S.; Combs, D.; Lev, D. A.; Schneider, C.; Rideout, M.; Meyer, C.; Hernandez, G.; Mejorado, L J. Org. Chem. 2002, 67, 9200.
13. (d) Bishop, B. B.; Brands, K. M. J.; Gibb, A. D.; Kennedy, D. J. Synthesis 2004, 43.
14. For reviews concerning tandem reactions: (a) Wasike, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
15. (b) Tieze, L. F. Chem. Rev. 1996, 96, 115.
16. (c) Negichi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
17. The reaction at room temperature for 24 h afforded 22% of noncarbonylative Sonogashira coupling product.
18. Melting points of 4ac (136-137°C (lit. 135-137°C)) and 4ca (68-69°C (lit. 70-72°C)) indicated exclusive formation of each product. See also Supporting Information.
19. (a) Mori, A.; Mohamed Ahmed, M. S.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756.
20. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
21. (c) Campbell, I. B. The Sonogashira Cu-Pd-catalyzed alkyne coupling reaction. In Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; pp 217-235.
22. The reaction with potassium carbonate resulted in giving the corresponding isoxazole (26% yield) accompanied by the noncarbonylative Sonogashira coupling product (20%).
23. (a) Johnston, K. M.; Shotter, R. G. J. Chem. Soc. C 1968, 1774.
24. (b) Linderman, R. J.; Kirollos, K. S. Tetrahedron Lett. 1989, 30, 2049.
25. (c) Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J.; Tang, L. T. J. Chem. Soc., Perkin Trans, 1 2000, 2311.
26. Although the reaction occasionally afforded a crude mixture of 5-hydroxyisoxazoline and 5, the isoxazoline was converted to 5 during isolation and purification procedures.