K 2CO 3-catalyzed synthesis of chromones and 4-quinolones through the cleavage of aromatic C-O bonds

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2710-2713

  Zhao, Jie ^a   Zhao, Yufen ^a,b   Fu, Hua ^a  

^a TSINGHUA UNIVERSITY   (China)

^b XIAMEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4 QUINOLONE DERIVATIVE; CARBONIC ACID DERIVATIVE; CHROMONE DERIVATIVE; PHENOL DERIVATIVE; POTASSIUM; POTASSIUM CARBONATE;

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

4-QUINOLONES; CARBONATES; CATALYSIS; CHROMONES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; MOLECULAR STRUCTURE; PHENOLS; POTASSIUM;

EID: 84861795576     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300908g     Document Type: Article

References (35)

1. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
2. Diederich, F.; Stang, P. J., Eds. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1997.
3. Rosen, B. N.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346-1416
4. Rappoport, Z. The Chemistry of Phenols; Wiley-VCH: Weinheim, 2003.
5. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255-263
6. Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609-612
7. Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818-11819
8. Limmert, M. E.; Roy, A. H.; Hartwig, J. F. J. Org. Chem. 2005, 70, 9364-9370
9. Macklin, T. K.; Snieckus, V. Org. Lett. 2005, 7, 2519-2522
10. Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J. Am. Chem. Soc. 2009, 131, 17748-17749
11. Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449-4452
12. Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katauro, Y.; Kumada, M. Synthesis 1981, 1001-1003
13. Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 14468-14470
14. Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422-14423
15. Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J. Am. Chem. Soc. 2009, 131, 17748-17749
16. Sengupta, S.; Leite, M.; Raslan, D. S. J. Org. Chem. 1992, 57, 4066-4068
17. Antoft-Finch, A.; Blackburn, T.; Snieckus, V. J. Am. Chem. Soc. 2009, 131, 17750-17752
18. Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707
19. Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128, 16516-16517
20. Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486-1495
21. Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246-2247
22. Dankwardt, J. W. Angew. Chem., Int. Ed. 2004, 43, 2428-2432
23. Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem., Int. Ed. 2008, 47, 4866-4869
24. Sergeev, A. G.; Hartwig, J. F. Science 2011, 332, 439-443
25. Havsteen, B. H. Pharmacol. Ther. 2002, 96, 67-202
26. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930
27. deAzevedo, W. F.; Mueller-Dieckmann, H. J.; Schulze-Gahmen, U.; Worland, P. J.; Sausville, E.; Kim, S. H. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 2735-2740
28. Banerji, A.; Goomer, N. C. Synthesis 1980, 874
29. Hirao, I.; Yamaguchi, M.; Hamada, M. Synthesis 1984, 1076
30. Darses, S.; Jeffrey, J. P.; Genet, J. P.; Brayer, J. L.; Demoute, J. P. Tetrahedron Lett. 1996, 37, 3857-3860
31. Roglans, A.; Pla-Quintana, A.; Moreno-Mañas, M. Chem. Rev. 2006, 106, 4622-4643
32. Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046-6047
33. Zhao, J.; Zhao, Y.; Fu, H. Angew. Chem., Int. Ed. 2011, 50, 3769-3773
34. Anderson, V. E.; Osheroff, N. Curr. Pharm. Des. 2001, 7, 337-353
35. Ziegler, C. B.; Bitha, P.; Kuck, N. A.; Fenton, T. J.; Petersen, P. J.; Lin, Y. I. J. Med. Chem. 1990, 33, 142-146