Liquid-phase traceless synthesis of 3,5-disubstituted 1,2,4-triazoles

Synlett

Volumn , Issue 17, 2005, Pages 2595-2598

  Wang, Xi Cun ^a   Wang, Jun Ke ^a,b   Wu, Dong Qing ^b   Zong, Ying Xiao ^b  

^a NORTHWEST NORMAL UNIVERSITY   (China)

^b HEXI UNIVERSITY   (China)

Author keywords

1,2,4 triazoles; Cyclization reaction; Lawesson's reagent; Soluble polymer; Traceless cleavage

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; BENZALDEHYDE; MACROGOL 6000; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; SYNTHESIS;

EID: 27444442251     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917107     Document Type: Article

References (30)

1. (a) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 55, 17.
2. (b) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549.
3. (c) Dolle, R. E. J. Comb. Chem. 2003, 5, 693.
4. (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
5. (b) Wentworth, P.; Janda, K. D. Chem. Commun. 1999, 1917.
6. (c) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546.
7. (a) Li, Z.; Wang, J. K.; Wang, X. C. Synth. Commun. 2003, 33, 3567.
8. (b) Wang, X. C.; Wang, J. K.; Li, Z. Chin. Chem. Lett. 2004, 15, 635.
9. (c) Wang, J. K.; Zong, Y. X.; An, H. G.; Xue, G. Q.; Wu, D. Q.; Wang, Y. S. Tetrahedron Lett. 2005, 46, 3797.
10. (d) Wang, J. K.; Zong, Y. X.; Yue, G. R. Synlett 2005, 1135.
11. (e) Wang, J. K.; Zong, Y. X.; Yue, G. R.; An, H. G.; Wang, X. C. J. Chem. Res., Synop. 2005, 335.
12. (a) Zhao, X.; Metz, W. A.; Sieber, F.; Janda, K. D. Tetrahedron Lett. 1998, 39, 8433.
13. (b) Blettner, C. G.; Konig, W. A.; Quhter, G.; Stenzel, W.; Schotten, T. Synlett 1999, 307.
14. (c) Racker, R.; Doring, K.; Reiser, O. J. Org. Chem. 2000, 65, 6932.
15. (d) Luisa, G.; Giorgio, M.; Pietro, C. J. Chem. Soc., Perkin Trans. 1 2002, 2504.
16. (a) Chen, C.; Dagnino, R.; Huang, C. Q.; McCarthy, J. R.; Grigoriadis, D. E. Bioorg. Med. Chem. Lett. 2001, 11, 3165.
17. (b) Jenkins, S. M.; Wadsworth, H. J.; Bromidge, S.; Orlek, B. S.; Wyman, P. A.; Riley, G. J.; Hawkins, J. J. Med. Chem. 1992, 35, 2392.
18. (a) Burrell, G.; Evans, J. M.; Hadley, M. S.; Hicks, F.; Stemp, G. Bioorg. Med. Chem. Lett. 1994, 4, 1285.
19. (b) Tully, W. R.; Gardner, C. R.; Gillepsie, R. J.; Westwood, R. J. Med. Chem. 1991, 34, 2060.
20. Duncia, J. V.; Santela, J. B. III; Higley, A.; VanAtten, M. K.; Weber, P. C.; Alexander, R. S.; Kettner, C. A.; Pruitt, J. R.; Liauw, A. Y.; Quan, M. L.; Knabb, R. M.; Wexler, R. R. Bioorg. Med. Chem. Lett. 1998, 8, 775.
21. Samanta, S. K.; Yli-Kauhaluoma, J. J. Comb. Chem. 2005, 7, 142.
22. Brunn, E.; Funke, E.; Gotthardt, H.; Huisgen, R. Chem. Ber. 1971, 104, 1562.
23. Hitostuyanagi, Y.; Motegi, S.; Fukaya, H.; Takeya, K. J. Org. Chem. 2002, 67, 3266.
24. Boeglin, D.; Cantel, S.; Heitz, A.; Martinez, J.; Fehrentz, J.-A. Org. Lett. 2003, 5, 4465.
25. Harju, K.; Vahermo, M.; Mutikainen, I.; Yli-Kauhaluoma, J. J. Comb. Chem. 2003, 5, 826.
26. Pietta, P. G.; Cavallo, P. F.; Takahashi, K.; Marshall, G. R. J. Org. Chem. 1974, 39, 44.
27. (a) Clausen, K.; Thorsen, M.; Lawesson, S. O. Tetrahedron 1981, 37, 3635.
28. (b) Majer, Z.; Zewdu, M.; Hollosi, M.; Seprodi, J.; Vadasz, Z.; Teplan, I. Biochem. Biophys. Res. Commun. 1988, 150, 1017.
29. (c) Pons, J. F.; Mishir, Q.; Nouvet, A.; Brookfield, F. Tetrahedron Lett. 2000, 41, 4965.
30. 3O: C, 63.05; H, 4.23; N, 14.71. Found: C, 63.17; H, 4.24; N, 14.68.