A catalytic route to ampakines and their derivatives

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1426-1428

  Mulzer, Michael ^a   Coates, Geoffrey W ^a  

^a Cornell University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; NOOTROPIC AGENT; OXAZINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CATALYSIS; COBALT; CYCLIZATION; MOLECULAR STRUCTURE; NOOTROPIC AGENTS; OXAZINES;

EID: 79952601626     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200111a     Document Type: Article

References (32)

1. Forman, M. S.; Trojanowski, J. Q.; Lee, V. M.-Y. Nat. Med. 2004, 10, 1055
2. Arai, A. C.; Kessler, M. Curr. Drug Targets 2007, 8, 583
3. O'Neill, M. J.; Bleackman, D.; Zimmerman, D. M.; Nisenbaum, E. S. CNS Neurol. Disord.: Drug Targets 2004, 3, 181
4. O'Neill, M. J.; Witkin, J. M. Curr. Drug Targets 2007, 8, 603
5. Yamada, K. A. Neurobiol. Disease 1998, 5, 67
6. Lynch, G. Curr. Opin. Pharmacol. 2006, 6, 82
7. Arai, A.; Kessler, M.; Ambros-Ingerson, J.; Quan, A.; Yigiter, E.; Rogers, G.; Lynch, G. Neuroscience 1996, 75, 573
8. Jourdi, H.; Hsu, Y.-T.; Zhou, M.; Qin, Q.; Bi, X.; Baudry, M. J. Neurosci. 2009, 29, 8688
9. Jin, R.; Clark, S.; Weeks, A. M.; Dudman, J. T.; Gouaux, E.; Partin, K. M. J. Neurosci. 2005, 25, 9027
10. Arai, A.; Kessler, M.; Rogers, G.; Lynch, G. Mol. Pharmacol. 2000, 58, 802
11. Dicoua, E.; Rangona, C.-M.; Guimiota, F.; Spedding, M.; Gressens, P. Brain Res. 2003, 970, 221
12. Jourdi, H.; Hamo, L.; Oka, T.; Seegan, A.; Baudry, M. Neuropharmacology 2009, 56, 876
13. Mueller, R.; Lee, S.; O'Hare, S.; Rogers, G.; Rachwal, S.; Street, L. US Pat. Appl. 2010/0041647 A1.
14. Rogers, G.; Lynch, G. Int. Pat. Appl. WO 97/36907.
15. Selected articles: Rowley, J. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2007, 129, 4948
16. Schmidt, J. A. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 11426
17. Byrne, C. M.; Church, T. L.; Kramer, J. W.; Coates, G. W. Angew. Chem., Int. Ed. 2008, 47, 3979
18. For a prior example of carbonylative ring expansion of 2-oxazolines, see: Xu, H.; Jia, L. Org. Lett. 2003, 5, 1575
19. Laitar, D. S.; Kramer, J. W.; Whiting, B. T.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2009, 5704
20. Böhme, H.; Böing, H. Arch. Pharm. 1961, 294, 556
21. Cayley, A. N.; Cox, R. J.; Ménard-Moyon, C.; Schmidt, J. P.; Taylor, R. J. K. Tetrahedron Lett. 2007, 48, 6556
22. Takacs, J. M.; Helle, M. A. Tetrahedron Lett. 1989, 30, 7321
23. Chiou, W.-H.; Mizutani, N.; Ojima, I. J. Org. Chem. 2007, 72, 1871
24. Tietze, L. F. Chem. Rev. 1996, 96, 115
25. Church, T. L.; Getzler, Y. D. Y. L.; Coates, G. W. J. Am. Chem. Soc. 2006, 128, 10125
26. 1H NMR spectroscopy or TLC analysis of the crude reaction mixture.
27. Saegusa, T.; Ikeda, H.; Fujii, H. Macromolecules 1973, 6, 315
28. Culbertson, B. M. Prog. Polym. Sci. 2002, 27, 579
29. Introduction of a methyl or phenyl group onto the oxygen-bearing methylene group led to low yields or a mixture of products, respectively.
30. Roe, C. D. Organometallics 1987, 6, 942
31. Ungváry, F.; László, M. Organometallics 1983, 2, 1608
32. -1. Attributing this peak to the cobalt-acyl species (cf. ref 15 and references therein), we suspect that the hydrogenolysis reaction might be the rate-determining step in our proposed catalytic cycle.