Reaction of β-dimethylaminovinyl ketones with hydroxylamine: A simple and useful method for synthesis of 3- and 5-substituted isoxazoles

Journal of Heterocyclic Chemistry

Volumn 45, Issue 3, 2008, Pages 879-885

  Rosa, Fernanda A ^a   Machado, Pablo ^a   Bonacorso, Helio G ^a   Zanatta, Nilo ^a   Martins, Marcos A P ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4 BROMOPHENYL)ISOXAZOLE; 3 (4 CHLOROPHENYL) 5 HYDROXY 4,5 DIHYDROISOXAZOLE; 3 (4 CHLOROPHENYL)ISOXAZOLE; 3 (4 FLUOROPHENYL)ISOXAZOLE; 3 (4 METNOXYPHENYL)ISOXAZOLE; 3 (4 NITROPHENYL) 5 HYDROXY 4,5 DIHYDROISOXAZOLE; 3 (4 NITROPHENYL)ISOXAZOLE; 3 DIMETHYLAMINO 1 (4 BROMOPHENYL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 (4 CHLOROPHENYL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 (4 FLUOROPHENYL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 (4 METHOXYPHENYL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 (4 NITROPHENYL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 (FUR 2 YL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 (PYRROL 2 YL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 (THIEN 2 YL) 2 PROPEN 1 ONE; 3 DIMETHYLAMINO 1 PHENYL 2 PROPEN 1 ONE; 3 PHENYL 5 HYDROXY 4,5 DIHYDROISOXAZOLE; 3 PHENYLISOXAZOLE; 4 DIMETHYLAMINO 1,1,1 TRICHLORO 3 BUTEN 2 ONE; 5 (4 CHLOROPHENYL)ISOXAZOLE; 5 (4 FLUOROPHENYL)ISOXAZOLE; 5 (4 METHOXYPHENYL)ISOXAZOLE; 5 (4 NITROPHENYL)ISOXAZOLE; 5 (FUR 2 YL)ISOXAZOLE; 5 DIMETHYLAMINO 4 PETEN 3 ONE; 5 PHENYLISOXAZOLE; HYDROXYLAMINE; ISOXAZOLE DERIVATIVE; KETONE DERIVATIVE; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 44349160128     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450337     Document Type: Article

References (28)

1. (a) Pevarello, P.; Amici, R.; Brasca, M. G.; Villa, M.; Varasi, M. Targets. Heterocycl. Sys. 1999, 3, 301-339.
2. (b) Perez, G. A.; Pillet, L.; Febvre, J.-C.; Lavault, S. WO Patent 2000025584, 2000; Chem. Abstr. 2000, 132, 304665.
3. Watts, R. E.; Siegel, M.; Khosla, C. J. Med. Chem. 2006, 49, 7493.
4. Conti, P.; Amici, M. De; Grazioso, G.; Roda, G.; Pinto, A.; Hansen, K. Bø; Nielsen, B.; Madsen, U.; Bräuner-Osborne, H.; Egebjerg, J.; Vestri, V.; Pellegrini-Giampietro, D. E.; Sibille, P.; Acher, F. C.; Micheli, C. De. J. Med. Chem. 2005, 48, 6315.
5. Frølund, B.; Jensen, L. S.; Storustovu, S. I.; Stensbøl, T. B.; Ebert, B.; Kehler, J.; Krogsgaard-Larsen, P.; Liljefors, T. J. Med. Chem. 2007, 50, 1988.
6. Patrick, D. A.; Bakunov, S. A.; Bakunova, S. M.; Kumar, E. V. K. S.; Lombardy, R. J.; Jones, S. K.; Bridges, A. S.; Zhirnov, O.; Hall, J. E; Wenzler, T.; Brun, R.; Tidwell, R. R. J. Med. Chem. 2007, 50, 2468.
7. Wünsch, K.-H.; Boulton, A. J. Adv. Heterocycl. Chem. 1967, 8, 277-379.
8. Grünanger, P.; Vita-Finzi, P. The Chemistry of Heterocyclic Compounds, Isoxazoles, Part 1, A. Weissenberg and E. C. Taylor, eds, Wiley-Interscience, New York, 1991.
9. Carr, J. B.; Durham, H. G.; Hass, D. K. J. Med. Chem. 1977, 20, 934.
10. Martins, M. A. P.; Cunico, W.; Pereira, C. M. P.; Sinhorin, A. P.; Flores, A. F. C.; Bonacorso, H. G.; Zanatta, N. Curr. Org. Synth. 2004, 1, 391 ; and references therein.
11. Wilson, R. D.; Burness, D. M. J. Org. Chem. 1966, 31, 1565.
12. Brederek, H.; Herlinger, H.; Schweizer, E. H. Chem. Ber. 1960, 93, 1208-1211.
13. Munno, A. De.; Bertini, V.; Lucchesini, F. J. Chem. Soc., Perkin Trans. 2 1977, 1121.
14. Lin, Y.-I.; Lang, S. A. J. Heterocycl.Chem. 1977, 14, 345.
15. Tseng, S-S.; Epstein, J. W.; Brabander, H. J.; Francisco, G. J. Heterocycl. Chem. 1987, 24, 837.
16. Chimichi, S.; Boccalini, M.; Hassan, M. M. M.; Viola, G.; Dall'Acqua, F.; Curini, M. Tetrahedron 2006, 62, 90.
17. Reidlinger, C.; Dworczak, R.; Junek, H. Monatsh. Chem. 1998, 129, 1207.
18. Al-Omram, F.; Elassar, A.-Z. A.; El-Khair, A. A. Tetrahedron 2001, 57, 10163.
19. Martins, M. A. P.; Zoch, A. N.; Flores, A. F. C.; Clar, G.; Zanatta, N.; Bonacorso, H. G. J. Heterocycl. Chem. 1995, 32, 739.
20. Martins, M. A. P.; Sinhorin, A. P.; Zimmermann, N. E. K.; Zanatta, N.; Bonacorso, H. G. Synthesis 2001, 1959.
21. Crystallographic data for struture (4d), reported in this paper, have been deposited with the Cambridge Crystallographic Data Center (CCDC 609434). Copies of the data can be obtained, free of charge, on application to CCDC 12 Union Road, Cambridge CB2 IEZ, UK (Fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
22. Molina, P.; Fresneda, P. M. J. Heterocycl. Chem. 1984, 21, 461.
23. Lin, Y.-I.; Lang, S. A. Jr. J. Org. Chem. 1980, 45, 4857.
24. Umada, A.; Okano, T.; Eguchi, S. Synthesis 1994, 1457.
25. (a) Tanaka, K.; Masuda, M.; Mitsuhashi, K. Bull. Chem. Soc. Jpn. 1984, 57, 2184.
26. (b) Kim, J. N.; Ryu, E. K. Heterocycles 1990, 31, 663.
27. Nunno, L. Di.; Scilimati, A. Tetrahedron 1987, 43, 2181.
28. Sosnovskikh, V. Ya.; Sizov, A. Yu.; Usachev, B. I. Russ. Chem. Bull., Int. Ed. 2002, 51, 1270.