Efficient and divergent synthesis of fully substituted 1H-pyrazoles and isoxazoles from cyclopropyl oximes

Organic Letters

Volumn 10, Issue 9, 2008, Pages 1691-1694

  Wang, Kewei ^a   Xiang, Dexuan ^a   Liu, Jinying ^a   Pan, Wei ^a   Dong, Dewen ^a,b  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLE DERIVATIVE; OXIME; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ISOXAZOLES; MOLECULAR STRUCTURE; OXIMES; PYRAZOLES;

EID: 48849112035     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800178x     Document Type: Article

References (60)

1. Penning, T.D.; Talley, J.J.; Bertenshaw, S. R,; Carter, J., S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers. R. S.; Rogier, D. J.; Yu, S.S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang. Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347-1365.
2. Terrett, N. K.; Bell. A. S.; Brown, D.; Ellis. P. Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824.
3. Elguero, J. In Comprenhensive Heterocyclic Chemistry II; Shinkai, I., Ed.; Elseiver; Oxford, U.K., 1996; Vol. 3, pp 3-75.
4. Elguero. J.; Goya, P.; Jagerovic, N.; Silva. A. M. S. Targets Heterocycl. Syst. 2002, 6, 52-98.
5. (a) Kost, A. N.; Grandberg, I. I. Adv. Heterocycl. Chem. 1966, 6, 347-429.
6. (b) Heller, S. T.; Natarajan, S. R. Org. Lett. 2006, 8, 2675-2678.
7. (c) Zefirov, N. S.; Kozhushkov. S. I.; Kuznetsova, T. S. Tetrahedron 1982, 38, 1693-1697.
8. (d) Kokoreva, O. V.; Averina, E. B.; Ivanova, O. A.; Kozhushkov, S. I.; Kuznetsova. T. S. Chem, Heterocycl. Comp. 2001, 37, 834-839.
9. (a) Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; John Wiley & Sons: New York, 1984; Vol. I.
10. (b) Martin, R.; Rodriguez Rivero, M.; Buchwald. S. L. Angew. Chem., Int. Ed. 2006, 45, 7079-7082.
11. (c) Aggarwal. V. K.; de Vicente, J.; Bonnert, R. V. J. Org. Chem. 2003, 68, 5381-5383.
12. (a) Talley, J. J. Prog. Med. Chem. 1999, 13, 201-234.
13. (b) Jaeger, V.; Colinas, P. A. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Chemistry of Heterocyclic Compounds; Wiley: Hoboken, NJ, 2002; Vol. 59, pp 361-472.
14. Mares. D.; Romagnoli, C; Tosi, B.; Benvegn, R.; Bruni. A.; Vicentini, C.B. Fungal Genet. Biol. 2002, 36, 47-57.
15. Wakefield, B. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Shaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 11, pp 229-288.
16. (a) Bandiera. T.; Grünanger. P.: Albini, F. M. J. Heterocycl. Chem. 1992, 29, 1423-1428.
17. (b) Zefirov, N. S.; Kozhushkov. S. I.; Kuznetsova, T. S.; Ershov, B.A.; Selivanov, S. I. Tetrahedron 1986, 42, 709-713.
18. (c) See refs 5c,d.
19. Vicentini, C. B.; Verones, A. C; Poli, T.; Guarneri, M.; Giori. P.; Ferretti, V. J. Hetercycl. Chem. 1990, 27, 1481-1484.
20. Cuadrado. P.; Gonzalez-Nogal, A. M.; Valero. R. Tetrahedron 2002, 58, 4975-4980.
21. Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203-5205.
22. (a) He, Y.; Lin. N.-H. Synthesis 1994, 989-992.
23. (b) Barber, G. N.; Olofson, R. A. J. Org. Chem. 1978, 43, 3015.
24. (c) Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828-5832.
25. (a) Denmark, S. E.; Kallemeyn, J. M. J. Org. Chem. 2005, 70, 2839-2842.
26. (b) Hansen, T. V.; Wu, P.; Fokin, V. V. J. Org. Chem. 2005, 70, 7761-7764.
27. For reviews, see:
28. (a) Danishefsky, S. Acc. Chem,. Res. 1979, 12, 66-72.
29. (b) Brackman, F.; de Meijere, A. Chem. Rev. 2007, 107, 4493-4537.
30. (c) Wong, H. N. C; Hon, M. Y.; Tse, C. W.; Yip, Y. C. Chem. Rev. 1989, 89, 165-198.
31. (d) Sydnes, L. K. Chem. Rev. 2003, 103, 1133-1150.
32. (e) Gnad, F.; Reiser. O. Chem. Rev. 2003, 103, 1603-1624.
33. (f) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196.
34. (g) Lebel, H.; Marcoux, J.-F.; Molinaro, C; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
35. (h) Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321-347.
36. (i) Reichelt, A.; Martin, S. F. Acc. Chem. Res. 2006, 39, 433-442.
37. For recent representative work, see: (a) Yadav, V. K.; Balamurugan, R. Org. Lett. 2001, 3, 2717-2719.
38. (b) Ma, S.; Zhang, J. Angew. Chem., Int. Ed. 2003, 42, 183-187.
39. (c) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565-4568.
40. (d) Ogoshi, S.: Nagata, M.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 5350-5351.
41. (e) Bowman, R. K.; Johnson, J. S. Org. Lett. 2006, 8, 573-576.
42. (f) Liu, L.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 5348-5349.
43. (g) Zhang. Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew. Chem., Int. Ed. 2007, 46, 1726-1729.
44. Pan. W.; Dong, D.; Wang, K.; Zhang, J.; Wu, R.; Xiang, D.; Liu, Q. Org. Lett. 2007, 9, 2421-2423.
45. (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578-4579.
46. (b) Dong, D.; Bi, X.; Liu, Q.; Cong, F. Chem. Commun. 2005, 3580-3582.
47. (c) Ouyang, Y.; Dong. D.; Yu, H.; Liang, Y.; Liu, Q. Adv. Synth, Catal. 2006, 348, 206-210.
48. (d) Xiang, D.; Yang, Y.; Zhang, R.: Liang, Y.; Pan, W.; Huang, J.: Dong, D. J. Org. Chem. 2007, 72, 8593-8596.
49. (a) Jutz, C. Iminium Salts in Organic Chemistry. In Advances in Organic Chemistry; Taylor, E. C.,. Ed.; John Wiley & Sons: New York, 1976; Vol. 9, Part I, pp 225-342.
50. (b) Meth-Cohn, O.; Tarnowski, B. Adv. Heterocycl. Chem. 1987,31, 207-236.
51. (c) Marson, C. M. Tetrahedron 1992, 48, 3659-3726.
52. (d) Jones, G.; Stanforth, S. P. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 49, pp 1-330.
53. (e) Meth-Cohn, O. Heterocycles 1993, 39, 539-557.
54. 3-mediated heteroannulations, see:
55. (a) Venkatesh, C; Singh. B.; Mahata, P. K.; Ila, H.; Junjappa, H. Org. Lett. 2005, 7, 2169-2172.
56. (b) Charles, I.: Latham, D. W. S.; Hartley, D.; Oxford, A. W.; Scopes. D. I. C. J. Chem. Soc., Perkin Trans. 1980, 1, 1139-1146.
57. (c) Gammon, D. W.; Hunter, R.; Wilson, S A. Tetrahedron 2005, 61, 10683-10688.
58. (a) Bernasconi, C. F. Tetrahedron 1989, 45, 4017-090.
59. (b) Bernasconi, C. F.; Schuck, D. F.; Ketner, R. J.; Eventova, 1.: Rappoport, Z. J. Am. Chem. Soc. 1995, 117, 2719-2725.
60. (c) Bernasconi, C. F.; Ketner, R. J.; Chen, X.; Rappoport, Z. J. Am. Chem. Soc. 1998, 120, 7461-7468.