A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants

Journal of Organic Chemistry

Volumn 73, Issue 23, 2008, Pages 9326-9333

  Nara, Susheel J ^a   Jha, Mukund ^a   Brinkhorst, Johan ^a   Zemanek, Tony J ^a   Pratt, Derek A ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; COPPER; PHENOLS;

ANTI-OXIDANTS; BENZYL ALCOHOLS; BENZYLAMINE; CATALYZED COUPLINGS; CHEMICAL EQUATIONS; SCAVENGING ABILITIES; SOLVENT EFFECTS;

ORGANIC POLYMERS;

3 HYDROXYPYRIDINE; 5 PYRIMIDINOL; ANTIOXIDANT; BENZYLAMINE; COPPER; PYRIMIDINONE DERIVATIVE; SCAVENGER; UNCLASSIFIED DRUG; ALPHA TOCOPHEROL; BENZENE; NITRILE; OXYGEN; PHENOL; PROPIONITRILE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROGENATION; STRUCTURE ACTIVITY RELATION; CHEMICAL MODEL; CHEMISTRY; KINETICS; TEMPERATURE;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; BENZENE; CATALYSIS; COPPER; KINETICS; MODELS, CHEMICAL; NITRILES; OXYGEN; PHENOL; PYRIDINES; PYRIMIDINES; TEMPERATURE;

EID: 57449084886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801501e     Document Type: Article

References (38)

1. (a) Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6472.
2. (b) Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194.
3. See, e.g.: Mahoney, L. R.; DaRooge, M. A J. Am. Chem. Soc. 1975, 97, 4722.
4. (b) Brigati, G.; Lucarini, M.; Mugaini, V.; Pedulli, G. F. J. Org. Chem. 2002, 67, 4828.
5. (c) Pratt, D. A.; DiLabio, G. A.; Mulder, P.; Ingold, K. U. Acc. Chem. Res. 2004, 37, 334.
6. (a) Burton, G. W.; Doba, T.; Gabe, E.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053.
7. (b) Barclay, L. R. C.; Vinqvist, M. R.; Mukai, K.; Itoh, S.; Morimoto, H. J. Org. Chem. 1993, 58, 7416.
8. (a) Pratt, D. A.; DiLabio, G. A.; Brigati, G.; Pedulli, G. F.; Valgimigli, L. J. Am. Chem. Soc. 2001, 123, 4625.
9. (b) Valgimigli, L.; Brigati, G.; Pedulli, G. F.; DiLabio, G. A.; Mastragostino, M.; Arbizzani, C.; Pratt, D. A. Chem. - Eur. J. 2003, 9, 4997.
10. (a) Wijtmans, M.; Pratt, D. A.; Valgimigli, L.; DiLabio, G. A.; Pedulli, G. F.; Porter, N. A. Angew. Chem., Int. Ed. 2003, 42, 4370.
11. (b) Wijtmans, M.; Pratt, D. A.; Brinkhorst, J.; Swerza, R.; Valgimigli, L.; Pedulli, G. F.; Porter, N. A. J. Org. Chem. 2004, 69, 9215.
12. See, e.g.: Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718.
13. See, e.g.: Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770.
14. Ullman, F. Chem. Ber. 1904, 37, 853.
15. For a general review, see: Lindley, J. Tetrahedron 1984, 40, 1433.
16. Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973.
17. Song, J. J.; Yee, N. K.; Tan, Z.; Xu, J.; Kapadia, S. R.; Senanayake, C. H. Org. Lett. 2004, 6, 4905.
18. Kaljurand, I.; Rodina, T.; Leito, I.; Koppel, I. A.; Schwesinger, R. J. Org. Chem. 2000, 65, 6202.
19. Albert, A.; Phillips, J. N. J. Chem. Soc. 1956, 1294.
20. Lützen, A.; Hapke, M.; Staats, H.; Bunzen, J. Eur. J. Org. Chem. 2003, 394, 8-3957.
21. Alternatively, one could envision a Pd-amination of the 6-halo-3-benzyloxypyridine to arrive at the 6-amino-3-benzyloxypyridine, but this approach is not useful for the pyrimidines, vide infra.
22. Crich, D.; Smith, M.; Yao, Q.; Picione, J. Synthesis 2001, 323.
23. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844.
24. Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
25. Siya, R.; Spicer, L. D. Synth. Commun. 1987, 17, 415.
26. Nam, P. C.; Nguyen, M. T.; Chandra, A. K. J. Phys. Chem. A 2006, 110, 10904.
27. Akao, A.; Nonoyama, N.; Yasuda, N. Tetrahedron Lett. 2006, 47, 5337.
28. Gutierrez, C. G.; Summerhays, L. R. J. Org. Chem. 1984, 49, 5206.
29. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737.
30. Roschek, B.; Tallman, K. A.; Rector, C. L.; Gillmore, J. G.; Pratt, D. A.; Punta, C.; Porter, N. A. J. Org. Chem. 2006, 71, 3527.
31. Jha, M.; Pratt, D. A. Chem. Comm. 2008, 1252.
32. Valgimigli, L.; Banks, J. T.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1999, 64, 3381.
33. MacFaul, P. A.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 1316.
34. Litwinienko, G.; Ingold, K. U. Acc. Chem. Res. 2007, 40, 222.
35. Steenken, S.; Neta, P. J. Phys. Chem. 1982, 86, 3661.
36. Cooper, T.; Nara, S. J.; Pratt, D. A., to be published.
37. Cherng, Y.-.J Tetrahedron 2002, 58, 4931-4935.
38. Seydel, J. J. Med. Chem. 1971, 14, 724-729.