Manipulation of N,O-nucleophilicity: Efficient formation of 4-N-substituted 2,4-dihydro-3H-1,2,4-triazolin-3-ones

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4795-4798

  Huang, Xianhai ^a   Palani, Anandan ^a   Xiao, Dong ^a   Aslanian, Robert ^a   Shih, Neng Yang ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; AMINE; AMMONIUM SULFATE; BROMOTRIMETHYLSILANE; CARBONYL DERIVATIVE; HEXAMETHYL DISILAZANE; SEMICARBAZIDE DERIVATIVE; SILANE DERIVATIVE; TRIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UREA;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 11444259663     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0478638     Document Type: Article

References (24)

1. (a) Michael, J.; Larson, S. B.; Vaghefi, M. M.; Robins, R. K. J. Heterocycl. Chem. 1990, 27, 1063.
2. (b) Haines, D. R.; Leonard, N. J.; Wiemer, D. F. J. Org. Chem. 1982, 47, 474.
3. Loev, B.; Musser, J. H.; Brown, R. E.; Jones, H.; Kahen, R.; Huang, F.-C.; Khandwala, A.; Sonnino-Goldman, P.; Leibowitz, M. J. Med. Chem. 1985, 28, 363.
4. Malbec, F.; Milcent, R.; Vicart, P. J. Heterocycl. Chem. 1984, 21, 1769.
5. Hrebabecky, H.; Beranek, J. Collect. Czech. Chem. Commun. 1985, 50, 779.
6. Chang, L. L.; Ashton, W. T.; Flanagan, K. L.; Chen, T.-B.; O'Malley, S. S.; Zingaro, G. J.; Kivlighn, S. D.; Siegl, P. K. S.; Lotti, V. J.; Chang, R. S. L.; Greenlee, W. J. Med. Chem. 1995, 38, 3741, and references therein.
7. Cowden, C. J.; Wilson, R. D.; Bishop, B. C.; Cottrel, I. F.; Davies, A. J.; Dolling, U.-H. Tetrahedron Lett. 2000, 41, 8661.
8. Chang, L. L.; Ashton, W. T.; Flanagan, K. L.; Rivero, R. A.; Chen, T.-B.; O'Malley, S. S.; Zingaro, G. J.; Kivlighn, S. D.; Siegl, P. K. S.; Lotti, V. J.; Chang, R. S. L.; Greenlee, W. J. Bioorg. Med. Chem. Lett. 1994, 4, 2787.
9. Madding, G. D.; Smith, D. W.; Sheldon, R. I.; Lee, B. J. Heterocycl. Chem. 1985, 22, 1121.
10. (a) Uneyamma, K.; Yamashita, F.; Sugimoto, K.; Morimoto, O. Tetrahedron Lett. 1990, 31, 2717.
11. (b) Moffett, R. B.; Kamdar, B. V. J. Heterocycl. Chem. 1979, 16, 793.
12. (c) Bartsch, H.; Erker, T. J. Heterocycl. Chem. 1988, 25, 1151.
13. (d) Bartsch, H.; Erker, T. J. Heterocycl. Chem. 1990, 27, 991.
14. (e) Grandolini, G.; Ambrogi, V.; Perioli, L. IL Farmaco 1996, 51, 203.
15. (f) Shapiro, R.; DiCosimo, R.; Hennessey, S. M.; Stieglitz, B.; Campopiano, O.; Chiang, G. C. Org. Proc. Res. Dev. 2001, 5, 593.
16. (a) Xu, Y.; Mayhugh, D.; Saeed, A.; Wang, X.; Thompson, R. C.; Dominianni, S. J.; Kauffman, R. F.; Singh, J.; Bean, J. S.; Bensch, W. R.; Barr, R. J.; Osborne, J.; Montrose-Rafizadeh, C.; Zink, R. W.; Yumibe, N. P.; Huang, N.; Luffer-Atlas, D.; Rungta, D.; Maise, D. E.; Mantlo, N. B. J. Med. Chem. 2003, 46, 5121.
17. (b) Tanoury, G. J.; Senanayake, C. H.; Hett, R.; Kuhn, A. M.; Kessler D. W.; Wald, S. A. Tetrahedron Lett. 1998, 39, 6845.
18. (c) Pachuta-Stec, A.; Dobosz, M. Acta Pol. Pharm. 2001, 58, 307.
19. (a) Langer, P.; Helmholz, F.; Schroeder, R. Synlett 2003, 2389.
20. (b) Vales, M.; Lokshin, V.; Pepe, G.; Guglielmetti, R.; Samat, A. Tetrahedron 2002, 58, 8543.
21. Herbert, J. M.; Woodgate, P. D.; Denny, W. A. J. Med. Chem. 1987, 30, 2081.
22. (a) Xiang, G.; McLaughlin, L. W. Tetrahedron 1998, 54, 375.
23. (b) Meng, G.; Chen, F.-E.; Clercq, E. D.; Balzarini, J.; Pannecouque, C. Chem. Pharm. Bull. 2003, 51, 779.
24. Langer, S. H.; Connell, S.; Wender, I. J. Org. Chem. 1958, 23, 50.