Soluble polymer-supported synthesis of pyrazoles via 1,3-dipolar cycloaddition strategy

Chinese Journal of Chemistry

Volumn 22, Issue 5, 2004, Pages 415-418

  Lin, Xu Feng ^a   Wang, Yan Guang ^a   Ding, Han Feng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

1,3 dipolar cycloaddition; Combinatorial chemistry; Liquid phase synthesis; Pyrazole; Soluble polymer

Indexed keywords

ALKENYL GROUP; ALKYNYL GROUP; MACROGOL; POLYMER; PYRAZOLE DERIVATIVE;

ARTICLE; COMBINATORIAL CHEMISTRY; CYCLOADDITION; ISOMERIZATION; OXIDATION; POLYMERIZATION; PURIFICATION; SOLUBILITY; SYNTHESIS;

EID: 3042733907     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20040220503     Document Type: Article

References (35)

1. Houk, K. N.; Sims, J.; Duke, R. E.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc. 1973, 95, 7287.
2. (a) Shen, D. M.; Shu, M.; Chapman, K. T. Org. Lett. 2000, 2, 2789.
3. (b) Stauffer, S. R.; Katzenellenbogen, J. A. J. Comb. Chem. 2000, 2, 318.
4. (c) Groshe, P.; Höltzel A.; Walk, T. B.; Trautwein, A. W.; Jung, G.; Synthesis 1999, 1961.
5. (d) Spivey, A. C.; Diaper, C. M.; Adams, H.; Rudd, A. J. J. Org. Chem. 2000, 65, 5253.
6. (e) Donohue, B. A.; Michelotti, E. L.; Reader, J. C.; Reader, V.; Stirling, M.; Tice, C. M. J. Comb. Chem. 2002, 4, 23.
7. (f) Stauffer, S. R.; Huang, Y.; Coletta, C. J.; Tedesco, R.; Katzenellenbogen, J. A. Bioorg. Med. Chem. 2001, 9, 141.
8. (g) Franzen, R. G. J. J. Comb. Chem. 2000, 2, 195.
9. (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
10. (b) Sun, C. M. Comb. Chem. High Throughput Screening 1999, 2, 299.
11. (c) Toy, P. H.; Tanda, K. D. Acc. Chem. Res. 2000, 33, 546.
12. (d) Wentworth, P.; Janda, K. D. Chem. Commun. 1999, 1917.
13. Nefzi, A.; Otresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449.
14. (a) Yeh, C. M.; Tung, C. L.; Sun, C. M. J. Comb. Chem. 2000, 2, 341.
15. (b) Zhao, X.; Metz, W. A.; Sieber, F.; Janda, K. D. Tetrahedron Lett. 1998, 39, 8433.
16. (c) Blettner, C. G.; Konig, W. A.; Quhter, G.; Stenzel, W.; Schotten, T. Synlett 1999, 307.
17. (d) Racker, R.; Doring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932.
18. (e) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem.-Eur. J. 2000, 6, 133.
19. (f) Lee, K. J.; Angulo, A.; Ghazal, P.; Janda, K. D. Org. Lett. 1999, 1, 1859.
20. (a) Shang, Y. J.; Wang, Y. G. Tetrahedron Lett. 2002, 43, 2247.
21. (b) Xia, M.; Wang, Y. G. Tetrahedron Lett. 2002, 43, 7703.
22. (c) Lin, X. F.; Zhang, J.; Wang, Y. G. Tetrahedron Lett. 2003, 44, 4113.
23. (d) Wang, Y. G.; Zhang, J.; Lin, X. F.; Ding, H. F. Synlett 2603, 1467.
24. 3, 500 MHz) δ: 3.82 (s, 3H), 7.19 (t, J = 8.5 Hz, 2H), 7.43-7.46 (m, 3H), 7.73-7.76 (m, 2H), 7.85 (d, J=6.5 Hz, 2H), 8.45 (s, 1H).
25. Alessandro, P.; Giorgio, M. J. Org. Chem. 2001, 66, 5252.
26. (a) Huisgen, R.; Seidel, M.; Wallbillich, G.; Knupfer, H. Tetrahedron 1962, 17, 3.
27. (b) Luisa, G.; Giorgio, M.; Pietro C. J. Chem. Soc., Perkin Trans. 1 2002, 2504.
28. (a) Gladstone, W. A. F.; Norman, R. O. C. J. Chem. Soc., Chem. Commun. 1966, 1536.
29. (b) Bhatnagar, I.; George, M. V. Tetrahedron 1968, 24, 1293.
30. (c) Auwers, K.; Heimke, P. Liebigs Ann. 1927, 458, 186.
31. (d) Smith, L. I.; Howard, K. L. J. Am. Chem. Soc. 1943, 65, 159.
32. (e) Dodwadmath, R. P.; Wheeler, T. S. Proc. Ind. Acad. Sci. 1935, 2A, 438.
33. (f) Singh, S. P.; Kumar, D.; Prakash, O.; Kapoor, R. P. Synth. Commun. 1997, 27, 2683.
34. Albert, P.; Michelle, A.; Donald, N. K.; Murphree, S. S.; Philip, E. Y. J. Org. Chem. 1993, 58, 2061.
35. +) 297.0961, found 297.0965.