Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones

Organic Letters

Volumn 16, Issue 13, 2014, Pages 3568-3571

  Manikandan, Rajendran ^a   Jeganmohan, Masilamani ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLOROQUINOLINE; 2-CHLOROQUINOLINE; ACRYLIC ACID DERIVATIVE; ANILIDE; BROMINATED HYDROCARBON; CHLORINATED HYDROCARBON; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE; RUTHENIUM;

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

ACRYLATES; ANILIDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; HYDROCARBONS, BROMINATED; HYDROCARBONS, CHLORINATED; MOLECULAR STRUCTURE; QUINOLINES; QUINOLONES; RUTHENIUM;

EID: 84903746733     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501548e     Document Type: Article

References (40)

1. Kraus, J. M.; Verlinde, C. L. M. J.; Karimi, M.; Lepesheva, G. I.; Gelb, M. H.; Buckner, F. S. J. Med. Chem. 2009, 52, 1639
2. Glasnov, T. N.; Stadlbauer, W.; Kappe, C. O. J. Org. Chem. 2005, 70, 3864
3. Claassen, G.; Brin, E.; Crogan-Grundy, C.; Vaillancourt, M. T.; Zhang, H. Z.; Cai, S. X.; Drewe, J.; Tseng, B.; Kasibhatla, S. Cancer Lett. 2009, 274, 243
4. Hassanin, H. M.; El-edfawy, S. M. Heterocycles 2012, 85, 2421
5. Michael, J. P. Nat. Prod. Rep. 1995, 12, 465
6. Hanuman, J. B.; Katz, A. Nat. Prod. Lett. 1993, 3, 227
7. Badgujar, N. S.; Pazicky, M.; Traar, P.; Terec, A.; Uray, G.; Stadlbauer, W. Eur. J. Org. Chem. 2006, 2715
8. Micotto, T. L.; Brown, A. S.; Wilson, J. N. Chem. Commun. 2009, 7548
9. Fabian, W. M. F.; Niederreiter, K. S.; Uray, G.; Stadlbauer, W. J. Mol. Struct. 1999, 477, 209
10. Anzini, M.; Cappelli, A.; Vomero, S. J. Heterocycl. Chem. 1991, 28, 1809
11. Godard, A.; Fourquez, J. M.; Tamion, R.; Marsais, F.; Queguine, G. Synlett 1994, 235
12. Domnguez-Fernandez, F.; Lopez-Sanz, J.; Perez-Mayoral, E.; Bek, D.; Martn-Aranda, R. M.; Lopez-Peinado, A. J.; Cejka, J. ChemCatChem. 2009, 1, 241
13. Marull, M.; Lefebvre, O.; Schlosser, M. Eur. J. Org. Chem. 2004, 54
14. Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2004, 69, 6772
15. Manley, P. J.; Bilodeau, M. T. Org. Lett. 2004, 6, 2433
16. Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516
17. Inamoto, K.; Saito, T.; Hiroya, K.; Doi, T. J. Org. Chem. 2010, 75, 3900
18. Ferguson, J.; Zeng, F.; Alwis, N.; Alper, H. Org. Lett. 2013, 15, 1998
19. Reddy, M. S.; Thirupathi, N.; Babu, M. H. Eur. J. Org. Chem. 2012, 5803
20. Huang, C.-C.; Chang, N.-C. Org. Lett. 2008, 10, 673
21. Angibaud, P. R.; Venet, M. G.; Filliers, W.; Broeckx, R.; Ligny, Y. A.; Muller, P.; Poncelet, V. S.; End, D. W. Eur. J. Org. Chem. 2004, 479
22. Gao, W.-T.; Hou, W.-D.; Zheng, M.-R.; Tang, L.-J. Synth. Commun. 2010, 40, 732
23. Thansandote, P.; Lautens, M. Chem.-Eur. J. 2009, 15, 5874
24. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
25. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
26. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
27. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
28. Ackermann, L. Acc. Chem. Res. 2014, 47, 281
29. Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764
30. Wang, L.; Ackermann, L. Org. Lett. 2013, 15, 176
31. Manikandan, R.; Jeganmohan, M. Org. Lett. 2014, 16, 912
32. Reddy, M. C.; Jeganmohan, M. Chem. Commun. 2013, 49, 481
33. Hashimoto, Y.; Hirano, K.; Satoh, T.; Kakiuchi, F.; Miura, M. Org. Lett. 2012, 14, 2058
34. Itoh, M.; Hashimoto, Y.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2013, 78, 8098
35. Baeumle, M. BioFiles 2011, 6.3, 23
36. Deng, Y.; Gong, W.; He, J.; Yu, J.-Q. Angew. Chem., Int. Ed. 2014, 10.1002/anie.201403878
37. Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728
38. Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. M. N. J. Am. Chem. Soc. 2002, 124, 1586
39. Manikandan, R.; Jeganmohan, M. Org. Lett. 2014, 16, 652
40. Kuninobu, Y.; Kawata, A.; Nishi, M.; Takata, Z.; Takai, K. Chem. Commun. 2008, 6360