Silver-mediated radical cyclization: Construction of δ2-isoxazolines from α-halo ketoximes and 1,3-dicarbonyl compounds

Chemical Communications

Volumn 50, Issue 52, 2014, Pages 6906-6908

  Liu, Yan Yun ^a   Yang, Xu Heng ^a   Yang, Ji ^a   Song, Ren Jie ^a   Li, Jin Heng ^a,b  

^a HUNAN UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; FREE RADICAL; HALOGENATED HYDROCARBON; ISOXAZOLE DERIVATIVE; OXIME; SILVER; 1,3 DIKETONE; ACETYLACETONE; CARBONYL DERIVATIVE; HYDROGEN; ISOXAZOLINE DERIVATIVE; PHENACYL CHLORIDE; RADICAL;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS; ARTICLE; CHEMICAL BOND; DECOMPOSITION; NUCLEOPHILICITY; REACTION ANALYSIS;

BENZENE DERIVATIVES; CYCLIZATION; FREE RADICALS; HYDROCARBONS, HALOGENATED; ISOXAZOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIMES; SILVER;

EID: 84901992422     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc02084g     Document Type: Article

References (58)

1. J. B. Sperry, D. Wright, Curr. Opin. Drug Discovery Dev., 2005, 8, 723.
2. P. K. Poutiainen, T. A. Venäläinen, M. Peräkylä, J. M. Matilainen, S. Väisänen, P. Honkakoski, R. Laatikainen, J. T. Pulkkinen, Bioorg. Med. Chem., 2010, 18, 3437.
3. N. Jullien, A. Makritis, D. Georgiadis, F. Beau, A. Yiotakis, V. Dive, J. Med. Chem., 2010, 53, 208.
4. S. Castellano, D. Kuck, M. Viviano, J. Yoo, F. López-Vallejo, P. Conti, L. Tamborini, A. Pinto, J. L. Medina-Franco, G. Sbardella, J. Med. Chem., 2011, 54, 7663.
5. K.-H. Hwang, J.-S. Lim, S.-H. Kim, M.-S. Jeon, D.-G. Lee, K.-H. Chung, S.-J. Koo, J.-H. Kim, J. Agric. Food Chem., 2013, 61, 9285.
6. A. P. Kozikowski, Acc. Chem. Res., 1984, 17, 410.
7. I. N. N. Namboothiri and N. Rastogi, Synthesis of Heterocycles via Cycloadditions I, in Topics in Heterocyclic Chemistry, ed. A. Hassner, Springer, Berlin, 2008, vol. 12, p. 1
8. D. P. Curran, S. A. Scanga, C. J. Fenk, J. Org. Chem., 1984, 49, 3474.
9. A. R. Minter, A. A. Fuller, A. K. Mapp, J. Am. Chem. Soc., 2003, 125, 6846.
10. K. N. Fleming, R. E. Taylor, Angew. Chem., Int. Ed., 2004, 43, 1728.
11. D. Muri, N. Lohse-Fraefel, E. M. Carreira, Angew. Chem., Int. Ed., 2005, 44, 4036.
12. A. M. Szpilman, D. M. Cereghetti, N. R. Wurtz, J. M. Manthorpe, E. M. Carreira, Angew. Chem., Int. Ed., 2008, 47, 4335.
13. B. J. D. Wright, J. Hartung, F. Peng, R. Van deWater, H. Liu, Q.-H. Tan, T.-C. Chou, S. J. Danishefsky, J. Am. Chem. Soc., 2008, 130, 16786.
14. F. Kleinbeck, E. M. Carreira, Angew. Chem., Int. Ed., 2009, 48, 578.
15. T. M. V. D. Pinho e Melo, Curr. Org. Chem., 2005, 9, 925.
16. V. Jäger and P. A. Colinas, in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, ed. A. Padwa, Wiley, Hoboken, 2002, vol. 59, p. 361
17. F. M. Cordero, D. Giomi and L. Lascialfari, in Progress in Heterocyclic Chemistry, ed. G. W. Gribble and J. A. Joule, Elsevier Ltd., 2013, vol. 25, p. 291.
18. L. Cecchi, F. De Sarlo, F. Machetti, Tetrahedron Lett., 2005, 46, 7877.
19. L. Cecchi, F. De Sarlo, F. Machetti, Eur. J. Org. Chem., 2006, 4852.
20. F. Machetti, L. Cecchi, E. Trogu, F. De Sarlo, Eur. J. Org. Chem., 2007, 4352.
21. L. Cecchi, F. De Sarlo, F. Machetti, Synlett, 2007, 2451.
22. L. Cecchi, F. De Sarlo, F. Machetti, Chem. Eur. J., 2008, 14, 7903.
23. E. Trogu, F. De Sarlo, F. Machetti, Chem. Eur. J., 2009, 15, 7940.
24. A. Pohjakallio, P. M. Pihko, J. Liu, J. Org. Chem., 2010, 75, 6712.
25. A. Singh, G. P. Roth, Org. Lett., 2011, 13, 2118.
26. S. Minakata, S. Okumura, T. Nagamachi, Y. Takeda, Org. Lett., 2011, 13, 2966.
27. E. Trogu, C. Vinattieri, F. De Sarlo, F. Machetti, Chem. Eur. J., 2012, 18, 2081.
28. E. Y. Schmidt, I. V. Tatarinova, E. V. Ivanova, N. V. Zorina, I. A. Ushakov, B. A. Trofimov, Org. Lett., 2013, 15, 104.
29. A. Yoshimura, K. R. Middleton, A. D. Todora, B. J. Kastern, S. R. Koski, A. V. Maskaev, V. V. Zhdankin, Org. Lett., 2013, 15, 4010.
30. M. Tiecco, L. Testaferri, L. Bagnoli, V. Purgatorio, A. Temperini, F. Marini, C. Santi, Tetrahedron: Asymmetry, 2001, 12, 3297.
31. H. A. Dondas, R. Grigg, M. Hadjisoteriou, J. Markandu, P. Kennewell, M. Thornton-Pett, Tetrahedron, 2001, 57, 1119.
32. V. Karapetyan, S. Mkrtchyan, T. T. Dang, A. Villinger, H. Reinke, P. Langer, Tetrahedron, 2008, 64, 8010.
33. M. D. Mosher, A. L. Norman, K. A. Shurrush, Tetrahedron Lett., 2009, 50, 5647.
34. M. Yonekawa, Y. Koyama, S. Kuwata, T. Takata, Org. Lett., 2012, 14, 1164.
35. C. B. Tripathi, S. Mukherjee, Angew. Chem., Int. Ed., 2013, 52, 8450.
36. D. Jiang, J. Peng, Y. Chen, Org. Lett., 2008, 10, 1695.
37. M.-K. Zhu, J.-F. Zhao, T.-P. Loh, J. Am. Chem. Soc., 2010, 132, 6284.
38. B. Han, X.-L. Yang, R. Fang, W. Yu, C. Wang, X.-Y. Duan, S. Liu, Angew. Chem., Int. Ed., 2012, 51, 8816.
39. R. K. Quinn, V. A. Schmidt, E. J. Alexanian, Chem. Sci., 2013, 4, 4030.
40. J. R. Thomas, J. Am. Chem. Soc., 1964, 86, 1446.
41. J. L. Brokenshire, G. D. Mendenhall, K. U. Ingold, J. Am. Chem. Soc., 1971, 93, 5278.
42. H. Lemaire, A. Rassat, Tetrahedron Lett., 1964, 5, 2245.
43. M. C. R. Symons, J. Chem. Soc., 1965, 2276.
44. W. M. Fox, M. C. R. Symons, J. Chem. Soc. A, 1966, 1503.
45. B. C. Gilbert, R. O. C. Norman, J. Chem. Soc. B, 1966, 86.
46. A. Mackor, J. Org. Chem., 1978, 43, 3241.
47. T. S. Dobashi, D. R. Parker, E. J. Grubbs, J. Am. Chem. Soc., 1977, 99, 5382.
48. G. D. Mendenhall, K. U. Ingold, J. Am. Chem. Soc., 1973, 95, 627.
49. M. Lucarini, G. F. Pedulli, A. Alberti, J. Org. Chem., 1994, 59, 1980.
50. B. M. Eisenhauer, M. Wang, H. Labaziewicz, M. Ngo, G. D. Mendenhall, J. Org. Chem., 1997, 62, 2050.
51. M. Naodovic, H. Yamamoto, Chem. Rev., 2008, 108, 3132.
52. J.-M. Weibel, A. Blanc, P. Pale, Chem. Rev., 2008, 108, 3149.
53. Silver in Organic Chemistry, ed. M. Harmata, John Wiley & Sons Inc., Hoboken, NJ, 2010
54. C. He, S. Guo, J. Ke, J. Hao, H. Xu, H. Chen, A. Lei, J. Am. Chem. Soc., 2012, 134, 5766.
55. M. Gao, C. He, H. Chen, R. Bai, B. Cheng, A. Lei, Angew. Chem., Int. Ed., 2013, 52, 6958.
56. X. Liu, Z. Wang, X. Cheng, C. Li, J. Am. Chem. Soc., 2012, 134, 14330.
57. J. Liu, Z. Fang, Q. Zhang, Q. Liu, X. Bi, Angew. Chem., Int. Ed., 2013, 52, 6953.
58. Y. Unoh, K. Hirano, T. Satoh, M. Miura, Angew. Chem., Int. Ed., 2013, 52, 12975.