Synthesis of 1,2,4-triazole-functionalized solid support and its use in the solid-phase synthesis of trisubstituted 1,2,4-triazoles

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1189-1191

  Katritzky, Alan R ^a   Qi, Ming ^a,b   Feng, Darning ^a   Zhang, Guifeng ^a   Griffith, Michael C ^b   Watson, Karen ^b  

^a University of Florida ^*  (United States)

^b Trega Biosciences Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001482825     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990186a     Document Type: Article

References (34)

1. (a) Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409.
2. (b) Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Tetrahedron 1991, 47, 2683.
3. (a) Katritzky, A. R.; Qi, M. J. Org. Chem. 1997, 62, 4116.
4. (b) Katritzky, A. R.; Qi, M.; Feng, D.; Nichols, D. A., J. Org. Chem. 1997, 62, 4121.
5. (a) Balkenhohl, F.; Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289.
6. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
7. (c) Acc. Chem. Res. 1996, 29, 111 (Special Issue on Combinatorial Chemistry; Czarnik, A. W., Ellman, J. A., Eds.).
8. (d) Chem. Rev. 1997, 97, 347 (Combinatorial Chemistry; Szostak, J., Ed.).
9. (e) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.
10. (f) Wilson, S. R., Czarnik, A. W., Eds. Combinatorial Chemistry, Synthesis and Application: John Wiley & Sons: New York, 1997.
11. (a) Katritzky, A. R.; Jozwiak, A.; Lue, P.; Yannakopoulou, K.; Palenik, G. J.; Zhang, Z.-Y. Tetrahedron 1990, 46, 633.
12. (b) Katritzky, A. R.; El-Zemity, S.; Lang, H.; Kadous, E. A.; El-Shazly, A. M. Synth. Commun. 1996, 26, 357.
13. (c) A model study using 3,5-diphenyl-1,2,4-triazole instead of benzotriazole in the synthesis of 1,3-aminoether [cf. Katritzky, A. R.; Rachwal, S.; Rachwal, B.; Steel, P. J. J. Org. Chem. 1992, 57, 4932] has been carried out successfully in this laboratory.
14. While this paper was in the internal review process, our group and others prepared benzotriazole on solid support, as well as the solid-phase synthesis of 3-thio-1,2,4-triazoles, see: (a) Katritzky, A. R.; Belyakov, S. A.; Tymoshenko, D. O. J. Comb. Chem. 1999, J, 173.
15. (b) Schiemann, K.; Showalter, H. D. H. J. Org. Chem. 1999, 64, 4972.
16. (c) Paio, A.; Zaramella, A.; Ferritto, R.; Conti, N.; Marchioro, C.; Seneci, P. J. Comb. Chem. 1999, 1, 317.
17. (d) Wilson, M. W.; Hernandez, A. S.; Calvet, A. P.; Hodges, J. C. Mol. Diversity 1998, 3, 95.
18. (a) Temple, C., Jr. The Chemistry of Heterocyclic Compounds, Vol. 37; Montgomery, J. A., Ed.; 1981; p 41.
19. (b) Francis, J. E.; Gorczyca, L. A.; Mazzeuga, G. C.; Meckler, H. Tetrahedron Lett. 1987, 28, 5133.
20. (c) Kosmrlj, J.; Kocevar, M.; Polanc, S. Synlett 1996, 652.
21. 2O-0.1% TFA.
22. (a) Hughes, D. L. Org. React. 1992, 42, 355.
23. (b) Richter, L. S.; Gadek, T. R. Tetrahedron Lett. 1994, 35, 4705.
24. (c) Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789.
25. (d) Krchnak, V.; Flegelova, Z.; Weichsel, A. S.; Lebl, M. Tetrahedron Lett. 1995, 36, 6193.
26. An alternative route for the synthesis of resin 3 was also tried. However, the Mitsunobu reaction between Wang resin and 4-hydroxybenzoic hydrazide in DMSO/NMM gave a complex mixture, according to HPLC analysis.
27. 2 (2 × 50 mL) and dried under vacuum to afford acyl hydrazide resin 3. (iii) Ten bags ot resin 3 were added to a solution of benzamidine (40 mmol) in 2-methoxyethanol (80 mL), followed by 4 Å molecular sieves (7 g). The tea bags were heated at 100°C for 7 days, washed as for resin 2, and dried to give triazole resin 4a.
28. (a) Zhang, H.; Liao, L.; Guo, Q. Houji Huaxue, 1986, 108; Chem. Abstr. 1986, 105, 226456.
29. (a) Zhang, H.; Liao, L.; Guo, Q. Houji Huaxue, 1986, 108; Chem. Abstr. 1986, 105, 226456.
30. (b) Katritzky, A. R.; Kuzmierkiewicz, W.; Greenhill, J. V. Recl. Trav. Chim. Pays-Bas 1991, 110, 369.
31. Houghten, R. A. U.S. Patent 4,631,211, 1986.
32. (a) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171.
33. (b) Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999.
34. (c) Gayo, L. M.; Suto, M. J. Tetrahedron Lett. 1997, 38, 211.