Hg(OTf) 2-catalyzed vinylogous semi-pinacol rearrangement leading to 1,4-dihydroquinolines

Organic Letters

Volumn 14, Issue 5, 2012, Pages 1222-1225

  Namba, Kosuke ^a   Kanaki, Michika ^a   Suto, Hiroki ^a   Nishizawa, Mugio ^b   Tanino, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROQUINOLINE; 1,4-DIHYDROQUINOLINE; ALKANONE; MESYLIC ACID DERIVATIVE; PINACOLONE; QUINOLINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BUTANONES; CATALYSIS; MESYLATES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUINOLINES; VINYL COMPOUNDS;

EID: 84857844302     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2034492     Document Type: Article

References (38)

1. Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 5, Chapter 5.06, p 245.
2. Patil, N. T.; Singh, V. J. Organomet. Chem. 2011, 696, 419
3. Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689
4. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675
5. Jiang, F.; Wu, Z.; Zhang, W. Tetrahedron 2011, 67, 1501
6. Okuro, K.; Alper, H. Tetrahedron Lett. 2010, 51, 4959
7. Mancheno, D. E.; Thornton, A. R.; Stoll, A. H.; Kong, A.; Blakey, S. B. Org. Lett. 2010, 12, 4110
8. Han, Z.-Y.; Chen, Z.-H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 9182
9. Liu, X.; Lu, Y. Org. Lett. 2010, 12, 5592
10. Saito, A.; Kasai, J.; Fukaya, H.; Hanazawa, Y. J. Org. Chem. 2009, 74, 5644
11. Lee, J. I.; Youn, J. S. Bull. Korean Chem. Soc. 2008, 29, 1853
12. Kumar, K. H.; Muralidharan, D.; Perumal, P. T. Synthesis 2004, 63
13. Giera, D. S.; Schneider, C. Org. Lett. 2010, 12, 4884
14. Sizhuo, K. X.; Li, W. P.; Li, X.; Yang, Z.; An, X.; Guo, C.-C.; Tan, Z. Tetrahedron Lett. 2010, 51, 4466
15. Youn, S. W.; Pastline, S. J.; Sames, D. Org. Lett. 2004, 6, 581
16. Lu, Z.; Hu, C.; Guo, J.; Cui, Y.; Jia, Y. Org. Lett. 2010, 12, 480
17. Liu, P.; Huang, L.; Lu, Y.; Dilmeghani, M.; Baum, J.; Xiang, T.; Adams, J.; Tasker, A.; Larsen, R.; Faul, M. M. Tetrahedron Lett. 2007, 48, 2307
18. Lautens, M.; Tayama, E.; Herse, C. J. Am. Chem. Soc. 2005, 127, 72
19. Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587
20. Nakao, Y.; Ebata, S.; Yada, A.; Hiyama, T.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2008, 130, 12874
21. Santos, L. S.; Pilli, R. A. Synthesis 2002, 87
22. Namba, K.; Nakagawa, Y.; Yamamoto, H.; Imagawa, H.; Nishizawa, M. Synlett 2008, 1719
23. Watanabe, T.; Oishi, T.; Fujii, N.; Ohno, H. Org. Lett. 2007, 9, 4821
24. Yoshino, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 7494
25. Rabideau, P. W.; Marcinow, Z. Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1992; 42, pp 3-320.
26. Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523
27. Zhang, Q.-W.; Fan, C.-A.; Zhang, H.-J.; Tu, Y.-Q.; Zhao, Y.-M.; Gu, P.; Chen, Z.-M. Angew. Chem., Int. Ed 2009, 48, 8572
28. Wang, B.; Tu, Y.-Q. Acc. Chem. Res. 2011, 44, 1207
29. Clayden, J.; Hamilton, S. D.; Mohammed, R. T. Org. Lett. 2005, 7, 3673
30. Lin, H.; Ng, F. W.; Danishefsky, S. J. Tetrahedron Lett. 2002, 43, 549
31. Otsuji, Y.; Yutani, K.; Imoto, E. Bull. Chem. Soc. Jpn. 1971, 44, 520
32. Nishizawa, M.; Imagawa, H.; Yamamoto, H. Org. Biomol. Chem. 2010, 8, 511
33. Zhou, F.; Cao, Z.-Y.; Zhang, J.; Yang, H.-B.; Zhou, J. Chem. Asisan J. 2012, 7, 233
34. Cao, Z.-Y.; Zhang, Y.; Ji, C.-B.; Zhou, J. Org. Lett. 2011, 13, 3178
35. Ravindar, K.; Reddy, M. S.; Deslongchamps, P. Org. Lett. 2011, 13, 3178
36. Yamamoto, H.; Sasaki, I.; Hirai, Y.; Namba, K.; Imagawa, H.; Nishizawa, M. Angew. Chem., Int. Ed. 2009, 48, 1244
37. Namba, K.; Kaihara, Y.; Yamamoto, H.; Imagawa, H.; Tanino, K.; Williams, R. M.; Nishizawa, M. Chem.-Eur. J. 2009, 15, 6560
38. Addition of methanol to the methyl ketone moiety of 31 was assumed to induce the aromatization to give 32. For the spectral data of 32, see: Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M. O. Org. Lett. 2004, 6, 2741-2744