Microwave-assisted synthesis of 2,4,5-Triaryl-Imidazole; a novel thermally induced N-hydroxyimidazole N-O bond cleavage

Organic Letters

Volumn 6, Issue 14, 2004, Pages 2473-2475

  Sparks, Richard B ^a   Combs, Andrew P ^a  

^a Experimental Station   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; HEAT TREATMENT; MICROWAVE IRRADIATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 3242730586     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049124x     Document Type: Article

References (16)

1. Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
2. Kaddar, H.; Hamelin, J.; Benhaoua, H. J. Chem. Res. 1999, 718-719.
3. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223.
4. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
5. Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234.
6. Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J. L.; Petit, A. Tetrahedron 1999, 55, 10851-10870.
7. Hong, B.; Shr, Y.; Liao, J. Org Lett. 2002, 4, 663-666.
8. Tu, S.; Miao, C.; Gao, Y.; Fang, F.; Zhuang, Q.; Feng, Y.; Shi, D. Synlett 2004, 2, 255-258.
9. Boehm, J.; Smietana, J.; Sorenson, M.; Garigipati, R.; Gallagher, T.; Sheldrake, P.; Bradbeer, J.; Badger, A.; Laydon, J.; Lee, J.; Hillegass, L.; Griswold, D.; Breton, J.; Chabot-Fletcher, M.; Adams, J. J. Med. Chem. 1996, 39, 3929-3937.
10. Usyatinsky, A.; Khmelnitsky, Y. Tetrahedron Lett. 2000, 41, 5031-5034.
11. Bilodeau, M.; Cunningham, A. J. Org. Chem. 1998, 63, 2800-2801.
12. Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453-1456.
13. Gallagher, T. F.; Fier-Thompson, S. M.; Garigipati, R. S.; Sorenson, M. E.; Smietana, J. M.; Lee, D.; Bender, P. E.; Lee, J. C.; Laydon, J. T.; Griswold, D. E.; Chabot-Fletcher, M. C.; Breton, J. J.; Adams, J. L. Bioorg. Med. Chem. Lett. 1995, 5, 1171-1176.
14. Liverton, N. J.; Butcher, J. W.; Claiborne, C. F.; Claremon, D. A.; Libby, B. E.; Nguyen, K. T.; Pitzenberger; Selnick, H. G.; Smith, G. R.; Tebben, A.; Vacca, J. P.; Varga, S. L.; Agarwal, L.; Dancheck, K.; Forsyth, A. J.; Fletcher, D. S.; Frantz, B.; Hanlon, W. A.; Harper, C. F.; Hofsess, S. J.; Kostura, M.; Lin, J.; Luell, S.; O'Neill, E. A.; Orevillo, C. J.; Pang, M.; Parsons, J.; Rolande, A.; Sahly, Y.; Visco, D. M.; O'Keefe, S. J. J. Med Chem. 1999, 42, 2180-2190.
15. Purification of the desired compounds using either C18 silica or Dowex 50WX8-200 resin failed because of poor retention on the solid phase.
16. + 331.3.