Regioselective [5,5]-sigmatropic rearrangement reactions of aryl hydrazides

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2047-2050

  Kang, Hong Min ^a   Lim, Young Kwan ^a   Shin, In Jee ^a   Kim, Hee Yeon ^a   Cho, Cheon Gyu ^a  

^a Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33744741355     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060451+     Document Type: Article

References (29)

1. (a) Hoffman, A. W. Proc. R. Soc. (London) 1863, 12, 576.
2. (b) Dewar, M. J. S. In Molecular Rearrangement; de Mayo, P., Ed.; Interscience: New York, 1969; Vol. 1, p 323.
3. (c) Banthorpe, D. V. Chem. Rev. 1970, 70, 295.
4. (d) Olah, G. A.; Dunne, K.; Kelly, D. P.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 7438.
5. (e) Cox, R. A.; Buncel, E. In The Chemistry of the Hydrazo, Azo, and Azoxy Groups; Patai, S., Ed.; Wiley; New York, 1975; p 775.
6. (f) Bunton, C. A.; Rubin, R. J. J. Am. Chem. Soc. 1976, 98, 4236.
7. (g) Park, K. H.; Kang, J. S. J. Org. Chem. 1997, 62, 3794.
8. (h) Benniston, A. C.; Clegg, W.; Harriman, A.; Harrington, R. W.; Li, P.; Craig, S. Tetrahedron Lett. 2003, 44, 2665.
9. (a) Chen, R.-F.; Fan, Q.-L.; Zheng, C.; Huang, W. Org. Lett. 2005, 8, 203.
10. (b) Chan, K. L.; McKiernan, M. J.; Towns, C. R.; Holmes, A. B. J. Am. Chem. Soc. 2005, 127, 21, 7662.
11. (a) Popovic, Z. D.; Aziz, H. J. Appl. Phys. 2005, 98, 13510.
12. (b) Tung, C.-H.; Zhang, L.-P.; Li, Y.; Cao, H.; Tanimoto, Y. J. Am. Chem. Soc. 1997, 119, 5348.
13. (a) Cheng, J. D.; Shine, H. J. J. Org. Chem. 1975, 40, 703.
14. (b) Zhu-Ohlbach, A.; Gleiter, R.; Bleiter, R.; Schmidt, H. L.; Reda, T. Eur. J. Org. Chem. 1998, 11, 2409.
15. (c) Buncel, E. Can. J. Chem. 2000, 78, 1251.
16. 4 or from azobenzenes through Zn-mediated reduction process that are moderately effective only for symmetric hydrazobenzenes. (a) Feiring, A. E.; Auman, B. C.; Wonchoba, E. R. Macromolecules 1993, 26, 2779.
17. (b) Shine, H. J.; Trisler, J. C. J. Am. Chem. Soc. 1960, 82, 4054.
18. (a) Lee, K. S.; Lim, Y. K.; Cho, C. G. Tetrahedron Lett. 2002, 43, 7463.
19. (b) Lim, Y. K.; Lee, K. S.; Cho, C. G. Org. Lett. 2003, 5, 979.
20. (c) Lim, Y. K.; Pang, S. J.; Paik, S. U, Cho, C. G. Bull. Korean Chem. Soc. 2003, 24, 543.
21. (d) Lim, Y. K.; Choi, S.; Park, K. B.; Cho, C. G. J. Org. Chem. 2004, 69, 2603.
22. (e) Lim, Y. K.; Jung, J. W.; Lee, H. Cho, C. G. J. Org. Chem. 2004, 69, 5778.
23. (f) Kim, K. Y.; Shin, J. T.; Lee, K. S.; Cho, C. G. Tetrahedron Lett. 2004, 45, 117.
24. 3, and 5 mL of anhydrous toluene at rt. The reaction mixture was stirred for 30 min at rt and refluxed for 2 h. The resulting mixture was concentrated and purified by flash column chromatography (hexanes/EtOAc = 20: 1) to afford 389 mg of product 6b in 99% yield.
25. 2/EtOAc = 2: 1) to afford 59 mg of 7b in 76% yield.
26. 2 with 1,3-dibromobenzene according to Buchwald's conditions. Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
27. Park, K. H.; Park, M.-K.; Cho, Y. H. Bull. Korean. Chem. Soc. 1998, 19, 1090.
28. The Pd-catalyzed coupling reaction of 4 with 1-bromo-3-iodobenzene gave the coupling product in only 47% yield.
29. 13C NMR, IR, and HRMS.