Reactions of in situ generated N-Boc nitrones with aromatic and heteroaromatic Grignard reagents: Application to the synthesis of zileuton

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 2028-2031

  Guinchard, Xavier ^a   Denis, Jean Noël ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSTS; CHEMICAL REACTIONS;

GRIGNARD REAGENTS; ZILEUTON;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; BENZENESULFONIC ACID DERIVATIVE; GRIGNARD REAGENT; HYDROXYUREA; NITRONE DERIVATIVE; ORGANOMETALLIC COMPOUND; ZILEUTON;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; HYDROGENOLYSIS; SYNTHESIS;

EID: 41149155538     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7025838     Document Type: Article

References (42)

1. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302 and references cited therein.
2. (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
3. (b) Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon: Oxford, 1991; Vol. 2.
4. (a) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468.
5. (b) Weinreb, S. M. Top. Curr. Chem. 1997, 190, 131.
6. (c) Sisko, J.; Weinreb, S. M. J. Org. Chem. 1990, 55, 393.
7. (d) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696.
8. (e) Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75.
9. (f) Mecozzi, T.; Petrini, M. Tetrahedron Lett. 2000, 41, 2709.
10. (g) Mecozzi, T.; Petrini, M. Synlett 2000, 73.
11. (h) Ballini, R.; Petrini, M. Tetrahedron Lett. 1999, 40, 4449.
12. (i) Lee, K. Y.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2003, 44, 1231.
13. (j) Speekamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
14. (k) Petrini, M. Chem. Rev. 2005, 105, 3949.
15. (a) Hamer, J.; Macaluso, A. Chem. Rev. 1964, 64, 473.
16. (b) Merino, P. C. R. Chim. 2005, 8.
17. (c) Merino, P. In Science of Synthesis; Padwa, A., Ed.; Georg Thieme Verlag: Stuttgart, 2004; Vol. 27, Chapter 13, pp 511-580.
18. (d) Lombardo, M.; Trombini, C. Synthesis 2000, 759.
19. Merino, P. Targets Heterocycl. Syst. 2003, 7, 140.
20. Guinchard, X.; Vallée, Y.; Denis, J.-N. Org. Lett. 2005, 7, 5147.
21. Commercialy available from Sigma-Aldrich Co.
22. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224.
23. Selected references: (a) For bioactive indolic compounds, see: Gul, W.; Hamman, M. T. Life Sci. 2005, 78, 442 and references cited therein.
24. Alvarez, M.; Salas, M. Heterocycles, 1991, 32, 1391 and references cited therein.
25. (b) For bioactive thiophene-based compounds, see: Fedi, V.; Altamura, M.; Catalioto, R.-M.; Giannotti, D.; Giolitti, A.; Giuliani, S.; Guidi, A.; Harmat, N. J. S.; Lecci, A.; Meini, S.; Nannicini, R.; Pasqui, F.; Tramontana, M.; Triolo, A.; Maggi, C. A. J. Med. Chem. 2007, 50, 4793.
26. Filzen, G. F.; Bratton, L.; Cheng, X.-M.; Erasga, N.; Geyer, A.; Lee, C.; Lu, G.; Pulaski, J.; Sorenson, R. J.; Unangst, P. C.; Trivedi, B. K.; Xu, X. Bioorg. Med. Chem. Lett. 2007, 17, 3630.
27. Fournier dit Chabert, J.; Marquez, B.; Neuville, L.; Joucla, L.; Broussous, S.; Bouhours, P.; David, E.; Pellet-Rostaing, S.; Marquet, B.; Moreau, N.; Lemaire, M. Bioorg. Med. Chem. 2007, 15, 4482 and references cited therein.
28. Basha, A.; Henry, R.; McLaughlin, M. A.; Ratajczyk, J. D.; Wittenberger, S. J. J. Org. Chem. 1994, 59, 6103.
29. (a) McGill, K. A.; Busse, W. W. Lancet 1996, 348, 519.
30. (b) Brooks, D. W.; Carter, G. W. Search Anti-Inflammatory Drugs 1995, 129.
31. (c) Wenzel, S. E.; Kamada, A. K. Ann. Pharmacother. 1996, 30, 858.
32. Bell, R. L. Novel Inhib. Leukotrienes 1999, 235.
33. Lewis, R. A.; Austen, K. F.; Soberman, R. J. N. Engl. J. Med. 1991, 323, 645.
34. (a) Kolasa, T.; Brooks, D. W. Synth. Commun. 1993, 23, 743.
35. (b) Basha, A.; Ratajczyk, J. D.; Brooks, D. W. Tetrahedron Lett. 1991, 32, 3783.
36. (a) Hsiao, C.-N.; Kolasa, T. Tetrahedron Lett. 1992, 33, 2629.
37. (b) Rohloff, J. C.; Alfredson, T. V.; Schwartz, M. A. Tetrahedron Lett. 1994, 35, 1011.
38. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 2381.
39. Bodwell, G. J.; Li, J. Org. Lett. 2002, 4, 127.
40. (a) Guinchard, X.; Vallée, Y.; Denis, J.-N. J. Org. Chem. 2007, 72, 3972.
41. (b) Guinchard, X.; Vallée, Y.; Denis, J.-N. Org. Lett. 2007, 9, 3761 and references cited therein.
42. For a general review on bis(indole) alkaloids, see: Yang, C.-G.; Huang, H.; Jiang, B. Curr. Org. Chem. 2004, 8, 1691.