Palladium-catalyzed carbonylative cross-coupling with imines: A multicomponent synthesis of imidazolones

Journal of Organic Chemistry

Volumn 73, Issue 3, 2008, Pages 1135-1138

  Siamaki, Ali R ^a   Black, Daniel A ^a   Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOCONDENSATION; IMIDAZOLONES; KETOCARBAMATES; MULTICOMPONENT SYNTHESIS;

CARBON MONOXIDE; CHEMICAL REACTIONS; PALLADIUM;

CATALYST ACTIVITY;

CARBAMIC ACID DERIVATIVE; CARBON MONOXIDE; FORMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; IMIDAZOLONE DERIVATIVE; IMINE; ORGANOTIN COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; ONE POT SYNTHESIS; POLYMERIZATION; REACTION ANALYSIS;

CARBONIC ACID; CATALYSIS; CROSS-LINKING REAGENTS; IMIDAZOLES; IMINES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 38849110755     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701875b     Document Type: Article

References (36)

1. (a) Sheppeck, J. E., II; Glimore, J. L.; Tebben, A.; Xue, C.-B.; Liu, R.-Q.; Decicco, C. P.; Duan, J. J. W. Bioorg. Med. Chem. Lett. 2007, 17, 2769-2774.
2. (b) Lai, Z.; Yang. T.; Kim, Y. B.; Sielecki, T. M.; Diamond, M. A.; Strack, P.; Rolfe, M.; Caligiuri, M.; Benfield, P. A.; Auger, K. R.; Copleland, R. A. PNAS 2002, 99, 14734-14739.
3. (c) Schnettler, R. A.; Dage, R. C.; Grisar, J. M. J. Med. Chem. 1982, 25, 1477-1481.
4. (d) Bernhart, C. A.; Perreaut, P. M.; Ferrari, B. P.; Muneaux, Y. A.; Assens, J.-L. A.; Clement, J.; Haudricourt, F.; Muneaux, C. F.; Taillades, J. E.; Vignal, M.-A.; Gougat, J.; Guiraudou, P. R.; Lacour, C. A.; Roccon, A.; Cazaubon, C. F.; Breliere, J.-C.; Le Fur, G.; Nisato, D. J. Med. Chem. 1993, 36, 3371-3380.
5. (e) Naylor, E. M.; Parmee, E. R.; Colandrea, V. J.; Perkins, L.; Brockunier, L.; Candelore, M. R.; Cascieri, M. A.; Colwell, L. F., Jr.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Strader, C. D.; Tota, L.; Wang, P.-R.; Wyvratt, M. J.; Fisher, M. H.; Weber, A. E. Bioorg. Med. Chem. Lett. 1999, 9, 755-758.
6. (f) Reitz, D. B.; Garland, D. J.; Norton, M. B.; Collins, J. T.; Reinhard, E. J.; Manning, R. E.; Olins, G. M.; Chen, S. T.; Palomo, M. A.; McMahon, E. G. Bioorg. Med. Chem. Lett. 1993, 3, 1055-1060.
7. (g) Adres, J. I.; et al. Bioorg. Med. Chem. Lett. 2002, 12, 653-658.
8. (h) Carling, R. W.; Moore, K. W.; Moyes, C. R.; Jones, E. A.; Bonner, K.; Emms, F.; Marwood, R.; Patel, S.; Patel, S.; Fletcher, A. E.; Beer, M.; Sohal, B.; Pike, A.; Leeson, P. D. J. Med. Chem. 1999, 42, 2706-2715.
9. (a) Lee, S.-H.; Yoshida, K.; Matsushita, H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. J. Org. Chem. 2004, 69, 8829-8835.
10. (b) Plummer, C. W.; Finke, P. E.; Mills, S. G.; Wang, J.; Tong, X.; Doss, G. A.; Fong, T. M.; Lao, J. Z.; Schaeffer, M.-T.; Chen, J.; Shen, C.-P.; Stribling, D. S.; Shearman, L. P.; Strack, A. M.; Van der Ploeg, L. H. T. Bioorg. Med. Chem. Lett. 2005, 15, 1441-1446.
11. For example: (a) Butler, A. R.; Hussain, I. J. Chem. Soc., Perkin 2 1981, 310-316.
12. (b) Patek, M.; Weichsel, A. S.; Drake, B.; Smrcina, M. Synlett 2005, 8, 1322-1324.
13. For example: Duschinsky, R.; Dolan, L. A. J. Am. Chem. Soc. 1946, 68, 2350-2355.
14. (a) Pesquet, A.; Daïch, A.; van Hijtfe, L. J. Org. Chem. 2006, 71, 5303-5311.
15. (b) Wendeborn, S.; Winkler, T.; Foisy, I. Tetrahedron Lett. 2000, 41, 6387-6391.
16. (c) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416.
17. (d) Cheng, J.-F.; Kaiho, C.; Chen, M.; Arrhenius, T. Tetrahedron Lett. 2002, 43, 4571-4573.
18. Lee, S.-H.; Clapham, B.; Koch, G.; Zimmermann, J. Org. Lett. 2003, 5, 511-514.
19. Kondo, T.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1992, 1318-1319.
20. Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496-7497.
21. Representative examples: (a) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786-7787.
22. (b) Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880-2881.
23. (c) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc. 2004, 126, 468-469.
24. (d) Siamaki, A. R.; Arndtsen, B. A. J. Am. Chem. Soc. 2006, 128, 6050-6051.
25. (e) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081-8082.
26. (f) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473.
27. (g) Wie, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472-1483.
28. Davis, J. L.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed 2004, 43, 590-594.
29. (a) Lee, H. B.; Balasubramanian, B. Org. Lett. 2000, 2, 323-326.
30. (b) Bleicher, K. H.; Gerber, F.; Wüthrich, Y.; Alanine, A.; Capretta, A. Tetrahedron Lett. 2002, 43, 7687-7690.
31. (c) Claiborne, C. F.; Liverton, N. J.; Nguyen, K. T. Tetrahedron. Lett. 1998, 39, 8939-8942.
32. (d) Frantz, D. E.; Morency, L.; Soheili, A.; Murry, J. A.; Grabowski, E. J. J.; Tillyer, R. D. Org. Lett. 2004, 6, 843-846.
33. Dghaym, R. D.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2001, 40, 3228-3230.
34. 4NBr is added in order to keep the ligandless palladium catalyst in solution (see ref 10).
35. The structure of 5a was distinguished from its 1H-imidazol-2-ol tautomer by means of NOE, and HSQC NMR experiments, as well as IR spectral data; see the Supporting Information for details.
36. For review: Jackson, P. F.; Bullington, J. L. Curr. Top. Med. Chem. 2002, 2, 1011-1020.