Divergent synthesis of fully substituted isoxazoles and spiro-fused pyrazolin-5-ones from cyclopropyl oximes

Tetrahedron

Volumn 67, Issue 34, 2011, Pages 6347-6351

  Fu, Xiaolan ^a   Huang, Peng ^b   Zhou, Guangyuan ^b   Hu, Yinqiao ^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

4 (2 BROMOETHYL) 3 METHYL N PHENYL ISOXAZOL 5 AMINE; 7 METHYL 5 PHENYL 5,6 DIAZASPIRO[2 4]HEPT 6 EN 4 ONE; ACETONITRILE; CYCLOPROPYL OXIME; ISOXAZOLE DERIVATIVE; OXIME DERIVATIVE; POTASSIUM HYDROXIDE; PYRAZOLINE DERIVATIVE; SPIRO FUSED PYRAZOLIN 5 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CYCLIZATION; EXPERIMENTAL STUDY; PRIORITY JOURNAL; RING OPENING; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS; TANDEM KETOXAMINE TOSYLATION;

EID: 79960576706     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.136     Document Type: Article

References (73)

1. F. Balkenhohl, C. Von Dem Bussche-Hünnefeld, A. Lansky, and C. Zechel Angew. Chem., Int. Ed. 35 1996 2288 2337
2. R.E. Dolle J. Comb. Chem. 6 2004 623 679
3. G.M. Cragg, P.G. Grothaus, and D.J. Newman Chem. Rev. 109 2009 3012 3043
4. L. Carlsen, D. Döpp, H. Döpp, F. Duus, H. Hartmann, S. Lang-Fugmann, B. Schulze, R.K. Smalley, and B.J. Wakefield E. Schaumann, Houben-Weyl, Methods in Organic Chemistry Vol E8a 1992 Georg Thieme Stuttgart, Germany 45 204
5. A. Makaritis, D. Georgiadis, V. Dive, and A. Yiotakis Chem. - Eur. J. 9 2003 2079 2094
6. A. Lilienkampf, J. Mao, B. Wan, Y. Wang, S.G. Franzblau, and A.P. Kozikowski J. Med. Chem. 52 2009 2109 2118
7. A. Lilienkampf, M. Pieroni, B. Wan, Y. Wang, S.G. Franzblau, and A.P. Kozikowski J. Med. Chem. 53 2010 678 688
8. J. Mao, H. Yuan, Y. Wang, B. Wan, D. Pak, R. He, and S.G. Franzblau Bioorg. Med. Chem. Lett. 20 2010 1263 1268
9. C. Dallanoce, F. Frigerio, M. De Amici, S. Dorsch, K.-N. Klotz, and C. De Micheli Bioorg. Med. Chem. 15 2007 2533 2543
10. D. Castagnolo, F. Manetti, M. Radi, B. Bechi, M. Pagano, A. De Logu, R. Meleddu, M. Saddi, and M. Botta Bioorg. Med. Chem. 17 2009 5716 5721
11. A. Kimata, H. Nakagawa, R. Ohyama, T. Fukuuchi, S. Ohta, T. Suzuki, and N. Miyata J. Med. Chem. 50 2007 5053 5056
12. M.S. Chande, P.A. Barve, and V. Suryanarayan J. Heterocycl. Chem. 44 2007 49 53
13. S.N. Shelke, N.R. Dalvi, S.B. Kale, M.S. More, C.H. Gill, and B.K. Karale Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 46 2007 1174 1178
14. Y. Sogawa, A. Shimizugawa, T. Ohyama, H. Maeda, and K. Hirahara J. Pharmacol. Sci. 111 2009 317 321
15. M. Lautens, and A. Roy Org. Lett. 2 2000 555 557
16. M.M. Savant, A.M. Pansuriya, C.V. Bhuva, N. Kapuriya, A.S. Patel, V.B. Audichya, P.V. Pipaliya, and Y.T. Naliapara J. Comb. Chem. 12 2010 176 180
17. J.P. Waldo, and R.C. Larock Org. Lett. 7 2005 5203 5205
18. L. Barr, S.F. Lincoln, and C.J. Easton Chem. - Eur. J. 12 2006 8571 8580
19. S. Grecian, and V.V. Fokin Angew. Chem., Int. Ed. 47 2008 8285 8287
20. L.F. Tietze, H. Evers, T. Hippe, A. Steinmetz, and E. Töpken Eur. J. Org. Chem. 2001 1631 1634
21. O.A. Attanasi, G. Baccolini, C. Boga, L. De Crescentini, G. Giorgi, F. Mantellini, and S. Nicolini Eur. J. Org. Chem. 2008 5965 5973
22. O.A. Attanasi, L. De Crescentini, P. Filippone, E. Foresti, and F. Mantellini J. Org. Chem. 65 2000 2820 2823
23. S. Danishefsky Acc. Chem. Res. 12 1979 66 72
24. H.N.C. Wong, M.-Y. Hon, C.-W. Tse, and Y.-C. Yip Chem. Rev. 89 1989 165 198
25. H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151 1196
26. L.K. Sydnes Chem. Rev. 103 2003 1133 1150
27. A. Reichelt, and S.F. Martin Acc. Chem. Res. 39 2006 433 442
28. V.S. Korotkov, O.V. Larionov, A. Hofmeister, J. Magull, and A. De Merjere J. Org. Chem. 72 2007 7504 7510
29. M. Tanaka, M. Ubakata, T. Matsuo, K. Yasue, K. Matsumoto, Y. Kajimoto, T. Ogo, and T. Inaba Org. Lett. 9 2007 3331 3334
30. C.L. Morales, and B.L. Pagenkopf Org. Lett. 10 2008 157 159
31. T. Tsuritani, Y. Yamamoto, M. Kawasaki, and T. Mase Org. Lett. 11 2009 1043 1045
32. A.E. Hours, and J.K. Snyder Organometallics 27 2008 410 417
33. X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, and B. Li J. Am. Chem. Soc. 127 2005 4578 4579
34. D. Dong, X. Bi, Q. Liu, and F. Cong Chem. Commun. 2005 3580 3582
35. D. Xiang, Y. Yang, R. Zhang, Y. Liang, W. Pan, J. Huang, and D. Dong J. Org. Chem. 72 2007 8593 8596
36. D. Xiang, P. Huang, K. Wang, G. Zhou, Y. Liang, and D. Dong Chem. Commun. 2008 6236 6238
37. D. Xiang, K. Wang, Y. Liang, G. Zhou, and D. Dong Org. Lett. 10 2008 345 348
38. R. Zhang, D. Zhang, Y. Guo, G. Zhou, Z. Jiang, and D. Dong J. Org. Chem. 73 2008 9504 9507
39. Y. Wang, X. Xin, Y. Liang, Y. Lin, H. Duan, and D. Dong Adv. Synth. Catal. 351 2009 2217 2223
40. W. Pan, D. Dong, K. Wang, J. Zhang, R. Wu, D. Xiang, and Q. Liu Org. Lett. 9 2007 2421 2423
41. R. Zhang, Y. Liang, G. Zhou, K. Wang, and D. Dong J. Org. Chem. 73 2008 8089 8092
42. K. Wang, D. Xiang, J. Liu, W. Pan, and D. Dong Org. Lett. 10 2008 1691 1694
43. K. Wang, X. Fu, J. Liu, Y. Liang, and D. Dong Org. Lett. 11 2009 1015 1018
44. R. Appel Angew. Chem., Int. Ed. Engl. 14 1975 801 811
45. 4, see: B. Das, B.S. Kanth, K.R. Reddy, G. Satyalakshmi, and R.A. Kumar Chem. Lett. 37 2008 512 513
46. M. Ori, N. Toda, K. Takami, K. Tago, and H. Kogen Angew. Chem., Int. Ed. 42 2003 2540 2543
47. Z. Wang, W. Wan, H. Jiang, and J. Hao J. Org. Chem. 72 2007 9364 9367
48. T. Morwick, M. Hrapchak, M. De Turi, and S. Campbell Org. Lett. 4 2002 2665 2668
49. 4, see: B. Das, K. Damodar, N. Bhunia, and B. Shashikanth Tetrahedron Lett. 50 2009 2072 2074
50. S.G. Gouin, and J. Kovensky Tetrahedron Lett. 48 2007 2875 2879
51. J.S. Yadav, and R.K. Mishra Tetrahedron Lett. 43 2002 5419 5422
52. Y. Nishida, Y. Shingu, H. Dohi, and K. Kobayashi Org. Lett. 5 2003 2377 2380
53. Y.-H. Yang, and M. Shi Tetrahedron 62 2006 2420 2427
54. Y.-H. Yang, and M. Shi J. Org. Chem. 70 2005 8645 8648
55. Y.-H. Yang, and M. Shi Tetrahedron Lett. 46 2005 6285 6288
56. K.M. Brummond, and K.D. Gesenberg Tetrahedron Lett. 40 1999 2231 2234
57. G. Lai, P.-Z. Tan, and P. Ghoshal Synth. Commun. 33 2003 1727 1732
58. R.P. Nair, T.H. Kim, and B.J. Frost Organometallics 28 2009 4681 4688
59. A. Khalafi-Nezhad, A. Parhami, M.N.S. Rad, and A. Zarea Tetrahedron Lett. 46 2005 6879 6882
60. F. Kazemi, H. Sharghi, and M.A. Nasseri Synthesis 2004 205 207
61. M.C. Pirrung, and L.N. Tumey J. Comb. Chem. 2 2000 675 680
62. K. Wakasugi, A. Iida, T. Misaki, Y. Nishii, and Y. Tanabe Adv. Synth. Catal. 345 2003 1209 1214
63. A.R. Katritzky, M. Wang, C.R. Wilkerson, and H. Yang J. Org. Chem. 68 2003 9105 9108
64. T.J. Dale, and A.C. Sather Jr. Tetrahedron Lett. 50 2009 6173 6175
65. P.D. Corce, and D. Pocar J. Chem. Soc., Perkin Trans. 1 1976 620 622
66. Z. Ren, W. Cao, J. Chen, Y. Chen, H. Deng, M. Shao, and D. Wu Tetrahedron 64 2008 5156 5161
67. A.N.R. Alba, A. Zea, G. Valero, T. Calbet, M. Font-Bardía, A. Mazzanti, A. Moyano, and R. Rios Eur. J. Org. Chem. 2011 1318 1325
68. R.E. Sammelson, C.D. Gurusinghe, J.M. Kurth, M.M. Olmstead, and M.J. Kurth J. Org. Chem. 67 2002 876 882
69. W. Holzer, R.M. Claramunt, M. Perez-Torralba, D. Guggi, and T.H. Brehmer J. Org. Chem. 68 2003 7943 7950
70. H. Wamhoff, and S.M.S. Atta Chem.-Ztg. 108 1984 285 286
71. H. Wamhoff, and F. Korte Chem. Ber. 99 1966 2962 2970
72. E. Magnien, and W. Tom J. Org. Chem. 32 1967 1229 1230
73. For the preparation of 5a from hydrazine and its analytical data, see: K.V. Auwers, and F. Dersch Justus Liebigs Ann. Chem. 462 1928 104 134