Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Facile Access to a Variety of 2,5-Biaryl-1,2,4-triazol-3-ones via Regioselective N-Arylation of Triazolones

  • Park, Ji-Yeon (Department of Chemistry and Institute of Basic Sciences, Sungshin Women's University) ;
  • Chae, Jung-Hyun (Department of Chemistry and Institute of Basic Sciences, Sungshin Women's University)
  • Received : 2010.05.19
  • Accepted : 2010.06.04
  • Published : 2010.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

A selective synthetic method of the 2,5-biaryltriazolones has been developed via copper-catalyzed N-arylation reaction. Aryltriazolones, which were readily prepared from commercially available compounds, were N-arylated to 2,5-biaryltriazolones with high regioselectivity. This approach allows for access to a variety of 2,5-biaryl-1,2,4-trizol-3-ones in a simple and practical manner.

Keywords

References

  1. Heers, J.; Back, J. J.; Cutsem, J. V. J. Med. Chem. 1984, 27, 894. https://doi.org/10.1021/jm00373a015
  2. Mullican, M. D.; Wilson, M. W.; Connor, D. T.; Kostlan, C. R.; Schrier, D. J.; Dyer, D. D. J. Med. Chem. 1993, 36, 1090. https://doi.org/10.1021/jm00060a017
  3. Neslihan, D.; Reyhan, U.; Ahmet, D. Bioorg. Med. Chem. 2002, 10, 3717. https://doi.org/10.1016/S0968-0896(02)00420-0
  4. Xu, Y.; Mayhugh, D.; Saeed, A.; Wang, X.; Thompson, R. C.; Dominianni, S. J.; Kauffman, R. F.; Sing, J.; Bean, J. S.; Bensch, W. R.; Barr, R. J.; Osborne, J.; Montrose-Rafizadeh, C.; Zink, R. W.; Yumibe, N. P.; Huang, N.; Luffer-Atllas, D.; Rungta, D.; Maise, D. E.; Mantlo, N. B. J. Med. Chem. 2003, 46, 5121. https://doi.org/10.1021/jm034173l
  5. Cowden, C. J.; Wison, R. D.; Bishop, B. C.; Cottrell, I. F.; Davies, A. J.; Dollong, U. Tetrahedron Lett. 2000, 41, 8661. https://doi.org/10.1016/S0040-4039(00)01548-3
  6. Romine, J. L.; Martin, S. W.; Meanwell, N. A.; Gribkoff, V. K.; Boissard, C. G.; Dworetzky, S. I.; Natale, J.; Moon, S.; Ortiz, A.; Yeleswaram, S.; Pajor, L.; Gao, Q.; Starrett, J. E., Jr. J. Med. Chem. 2007, 50, 528. https://doi.org/10.1021/jm061006n
  7. Romine, J. L.; Martin, S. W.; Gribkoff, V. K.; Boissard, C. G.; Dworetzky, S. I.; Natale, J.; Li, Y.; Gao, Q.; Meanwell, N. A.; Starrett, J. E., Jr. J. Med. Chem. 2002, 45, 2942. https://doi.org/10.1021/jm010569q
  8. Hewawasam, P.; Erway, M.; Thalody, G.; Weiner, H.; Boissard, C. G.; Gribkoff, V. K.; Meanwell, N. A.; Lodge, N.; Starrett, J. E., Jr. Bioorg. Med. Chem. Lett. 2002, 12, 1117. https://doi.org/10.1016/S0960-894X(02)00099-9
  9. Ying, W.; Przewloka, T.; Chae, J.; Zhang, S.; Li, H.; Du, Z.; James, D.; Chimmanamada, D. U.; Ng, H. P.; Foley, K.; Demko, Z.; Sun, L.; Zhou, D.; Qin, S. U.S. Patent 20080176840, 2008.
  10. Lee, C.; James, D.; Zhang, S.; Ying, W.; Chimmanamada, D.; Chae, J.; Przewloka, T. U.S. Patent 20080125587, 2008.
  11. Chae, J.; Demko, Z.; Ying, W.; Du, Z.; Foley, K.; James, D.; Ptzewloka, T.; Song, M.; Zhang, S.; Ng, H. P.; Li, H.; Chimmanamada, D. U.; Zhou, D.; Qin, S.; Lee, C.; Sun, L.; Koya, K. U.S. Patent 2008090887, 2008.
  12. Ohsumi, K.; Hatanaka, T.; Fujita, K.; Nakagawa, R.; Fukuda, Y.; Nihei, Y.; Suga, Y.; Morinaga, Y.; Akiyama, Y.; Tsuji, T. Bioorg. Med. Chem. Lett. 1998, 8, 3153. https://doi.org/10.1016/S0960-894X(98)00579-4
  13. Noto, R.; Gruttadauria, M.; Lo Meo, P.; Frenna, V.; Werber, G. J. Heterocyclic Chem. 1995, 32, 1277. https://doi.org/10.1002/jhet.5570320430
  14. Gruttadauria, M.; Buccheri, F.; Cusmano, G.; Lo Meo, P.; Noto, R.; Werber, G. J. Heterocyclic Chem. 1993, 30, 765. https://doi.org/10.1002/jhet.5570300327
  15. Milcent, R.; Nguyen, T. H. J. Heterocyclic Chem. 1986, 23, 881. https://doi.org/10.1002/jhet.5570230343
  16. Nguyen, T. H.; Milcent, R.; Barbier, G. J. Heterocyclic Chem. 1985, 22, 1383. https://doi.org/10.1002/jhet.5570220552
  17. Deng, J. Z.; Burgey, C. S. Tetrahedron Lett. 2005, 46, 7993. https://doi.org/10.1016/j.tetlet.2005.09.073
  18. Lin, S.; Liu, S. X.; Huang, J. Q.; Lin, C. C. J. Chem. Soc. Dalton Trans. 2002, 8, 1595.
  19. Mazzone, G.; Puglisi, G.; Corsaro, A.; Panico, A.; Bonina, F.; Amico-Roxas, M.; Caruso, A.; Trombadore, S. Eur. J. Med. Chem. 1986, 21, 277.
  20. George, B.; Papadopoulos, E. P. J. Org. Chem. 1976, 41, 3233 https://doi.org/10.1021/jo00882a003
  21. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. https://doi.org/10.1007/3-540-45313-X_5
  22. Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; John Wiley & Sons: Weinheim, 2004; p 699.
  23. Christmann, U.; Vilar, R. Angew. Chem. Int. Ed. 2005, 44, 366. https://doi.org/10.1002/anie.200461189
  24. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400. https://doi.org/10.1002/anie.200300594
  25. Kunz, K.; Scholz, U.; Ganzer, D. Synlett. 2003, 2428.
  26. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337. https://doi.org/10.1016/j.ccr.2004.09.014
  27. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. https://doi.org/10.1021/ja0260465
  28. Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803. https://doi.org/10.1021/ol0168216
  29. Chae, J.; Buchwald, S. L. J. Org. Chem. 2004, 69, 3336. https://doi.org/10.1021/jo035819k
  30. Wang, Z.; Skerlj, R. T.; Bridger, G. J. Tetrahedron Lett. 1999, 40, 3543. https://doi.org/10.1016/S0040-4039(99)00561-4

Cited by

  1. ChemInform Abstract: Facile Access to a Variety of 2,5‐Biaryl‐1,2,4‐triazol‐3‐ones via Regioselective N‐Arylation of Triazolones. vol.41, pp.52, 2010, https://doi.org/10.1002/chin.201052136