Palladium-catalyzed intermolecular cyclocarbonylation of 2-iodoanilines with the Michael acceptor, diethyl ethoxycarbonylbutendienoate

Journal of Organic Chemistry

Volumn 77, Issue 9, 2012, Pages 4420-4424

  Okuro, Kazumi ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOCARBONYLATION; MICHAEL ACCEPTORS; MICHAEL ADDITIONS; PALLADIUM-CATALYZED; QUINOLINONE DERIVATIVES;

ADDITION REACTIONS; CARBONYLATION;

CATALYSIS;

2 ACETYL 3,3 DIETHOXYCARBONYL 2,3 DIHYDRO 4(1H) QUINOLINONE; 2 CYANO 3,3 DIETHOXYCARBONYL 2,3 DIHYDRO 4(1H) QUINOLINONE; 2 TRIFLUOROMETHYL 3,3 DIETHOXYCARBONYL 2,3 DIHYDRO 4(1H) QUINOLINONE; 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 4(1H) QUINOLINONE; 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 6 METHOXY 4(1H) QUINOLINONE; 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 6 METHYL 4(1H) QUINOLINONE; 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 6,8 DIMETHYL 4(1H) QUINOLINONE; 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 7 METHOXY 4(1H) QUINOLINONE; 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 7 METHYL 4(1H) QUINOLINONE; 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 8 METHOXY 4(1H) QUINOLINONE; 6 CHLORO 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 4(1H) QUINOLINONE; 6,8 DICHLORO 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 4(1H) QUINOLINONE; 7 CHLORO 2,3,3 TRIETHOXYCARBONYL 2,3 DIHYDRO 4(1H) QUINOLINONE; ANALGESIC AGENT; ANILINE DERIVATIVE; ANTIMALARIAL AGENT; PALLADIUM; QUINOLINE DERIVED ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CONTROLLED STUDY; MICHAEL ADDITION;

ANILINE COMPOUNDS; BUTYRIC ACIDS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM; QUINOLONES;

EID: 84860617642     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300173g     Document Type: Article

References (37)

1. Atwal, M. S.; Bauer, L.; Dixit, S. N.; Gearien, J. E.; Morris, R. W. J. Med. Chem. 1965, 8, 566
2. La Montagne, M. P.; Blumbergs, P.; Smith, D. C. J. Med. Chem. 1989, 32, 1728
3. Gong, Y.; Kato, K. J. Fluorine Chem. 2004, 125, 767
4. Fargeau, B.; Claude, M.; Bernadette, G.; Sacquet, S. M.; Maitte, P. J. Heterocycl. Chem. 1985, 22, 713
5. Jarvest, R. L.; Berge, J. M.; Berry, V.; Boyd, H. F.; Brown, M. J.; Elder, J. S.; Forrest, A. K.; Fosberry, A. P.; Gentry, D. R.; Hibbs, M. J.; Jaworski, D. D.; O'Hanlon, P. J.; Pope, A. J.; Rittenhouse, S.; Sheppard, R. J.; Slater-Radosti, C.; Worby, A. J. Med. Chem. 2002, 45, 1959
6. Schmidt, R. G.; Bayburt, E. K.; Latshaw, S. P.; Koenig, J. R.; Daanen, J. F.; McDonald, H. A.; Bianchi, B. R.; Zhong, C.; Joshi, S.; Honore, P.; Marsh, K. C.; Lee, C.-H.; Faltynek, C. R.; Gomtsyan, A. Bioorg. Med. Chem. Lett. 2011, 21, 1338
7. Anderson, K. W.; Tepe, J. J. Tetrahedron 2002, 58, 8475
8. Kano, S.; Ebata, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1999, 10, 2105
9. Kundu, N. G.; Mathnty, J. S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625
10. Donnelly, J.; Farrell, D. Tetrahedron 1990, 46, 885
11. Richard, A. B.; Baskar, N. J. Heterocycl. Chem. 2011, 48, 613
12. Pisaneschi, F.; Sejberg, J. J. P.; Blain, C.; Ng, W. H.; Aboagye, E. O.; Spivey, A. Synlett 2011, 2, 241
13. Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7125
14. Nemoto, T.; Fukuda, T.; Hamada, Y. Tetrahedron Lett. 2006, 47, 4365
15. Vlaar, T.; Ruijter, E.; Orru, R. V. A. Adv. Synth. Catal. 2011, 353, 809
16. Bontemps, S.; Quesnel, J. S.; Worrall, K.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2011, 50, 8948
17. Li, Q.; Jiang, X.; Fu, C.; Ma, S. Org. Lett. 2011, 13, 466
18. Cao, H.; Jiang, H.; Huang, H. Synthesis 2011, 7, 1019
19. Yu, X.; Lu, X. Org. Lett. 2009, 11, 4366
20. Chouhan, G.; Alper, H. Org. Lett. 2008, 10, 4987
21. Zheng, Z.; Alper, H. Org. Lett. 2008, 10, 829
22. Larock, R. C. J. Organomet. Chem. 1999, 576, 111
23. Larock, R. C. Pure Appl. Chem. 1999, 71, 1435
24. Zheng, Z.; Alper, H. Org. Lett. 2009, 11, 3278
25. Zheng, Z.; Alper, H. Org. Lett. 2008, 10, 4903
26. Larksarp, C.; Alper, H. Org. Lett. 1999, 1, 1619
27. Zheng, Z.; Alper, H. Org. Lett. 2008, 10, 829
28. Chouhan, G.; Alper, H. Org. Lett. 2010, 12, 192
29. Zeng, F.; Alper, H. Org. Lett. 2010, 12, 5567
30. Yamazaki, S.; Yamamoto, M.; Sumi, A. Tetrahedron 2007, 63, 2320
31. Tsuji, J. Palladium Reagents and Catalysts; Wiley & Sons: Hoboken, NJ, 1995.
32. Kobayashi, T.; Tanaka, M. Tetrahedron Lett. 1986, 27, 4745
33. Negishi, E.; Zhang, Y.; Shimoyama, I.; We, G. J. Am. Chem. Soc. 1989, 111, 8018
34. Fujita, K.; Takahashi, Y.; Owaki, M.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2004, 6, 2785
35. Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507
36. Yamakawa, T.; Ideue, E.; Shimokawa, J.; Fukuyama, T. Angew. Chem, Int. Ed. 2010, 49, 9262
37. Blond, G.; Billard, T.; Langlois, B. R. J. Org. Chem. 2001, 66, 4826