Cu-catalyzed 1,2-dihydroisoquinolines synthesis from o-ethynyl benzacetals and sulfonyl azides

Organic Letters

Volumn 15, Issue 22, 2013, Pages 5894-5897

  Sun, Lang ^a   Zhu, Yuanxun ^a   Lu, Ping ^a   Wang, Yanguang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; AZIDE; COPPER; ISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; SYNTHESIS;

ACETALS; AZIDES; CATALYSIS; COPPER; CYCLOADDITION REACTION; ISOQUINOLINES; MOLECULAR STRUCTURE;

EID: 84887890738     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402996x     Document Type: Article

References (34)

1. Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341
2. Ramesh, P.; Reddy, N. S.; Venkateswarlu, Y. J. Nat. Prod. 1999, 62, 780
3. Mahmoud, S.; Aboul-Fadl, T.; Sheha, M.; Farag, H.; Mouhamed, A. I. Arch. Pharm. Pharm. Med. Chem. 2003, 336, 573
4. Su, Y. J.; Huang, H. L.; Li, C. L.; Chien, C. H.; Tao, Y. T.; Chou, P. T.; Datta, S.; Liu, R. S. Adv. Matter. 2003, 15, 884
5. Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: 2005; p 62.
6. Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: 2005; p 348.
7. Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: 2005; p 358.
8. Meziane, M. A. A. A.; Bazureau, J. P. Molecules 2002, 7, 252
9. Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 553
10. Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306
11. Ohtaka, M.; Nakamura, H.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 7339
12. Asao, N.; Yudha, S. S.; Nogami, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 5526
13. Asao, N.; Iso, K.; Yudha, S. S. Org. Lett. 2006, 8, 4149
14. Yanada, R.; Obika, S.; Kono, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3822
15. Chen, Z. Y.; Yang, X. D.; Wu, J. Chem. Commun. 2009, 3469
16. Sun, W.; Ding, Q. P.; Sun, X. Y.; Fan, R. H.; Wu, J. J. Comb. Chem. 2007, 9, 690
17. Obika, S.; Kono, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2007, 72, 4462
18. Gao, K.; Wu, J. J. Org. Chem. 2007, 72, 8611
19. Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
20. Lu, P.; Wang, Y. G. Chem. Soc. Rev. 2012, 41, 5687
21. Kim, S. H.; Park, S. H.; Choi, J. H.; Chang, S. Chem.-Asian J. 2011, 6, 2618
22. Lu, P.; Wang, Y. G. Synlett 2010, 2, 165
23. CCDC 965973 contains the supplementary crystallographic data for 3k. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
24. CCDC 965974 contains the supplementary crystallographic data for 5a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
25. Alajarín, M.; Bonillo, B.; Ortín, M. M.; Sánchez-Andrada, P.; Vidal, A. Org. Lett. 2006, 8, 5645
26. Alajarin, M.; Bonillo, B.; Ortin, M. M.; Sanchez-Andrada, P.; Vidal, A.; Orenes, R. A. Org. Biomol. Chem. 2010, 8, 4690
27. Alajarin, M.; Bonillo, B.; Ortin, M. M.; Sanchez-Andrada, P.; Vidal, A. Eur. J. Org. Chem. 2011, 1896
28. CCDC 965975 contains the supplementary crystallographic data for 6a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
29. Akiba, K.; Nakatani, M.; Wada, M.; Yamamoto, Y. J. Org. Chem. 1985, 50, 63
30. Wu, G. Z.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3238
31. Korivi, R. P.; Wu, Y. C.; Cheng, C. H. Chem.-Eur. J. 2009, 15, 10727
32. Jayakumar, J.; Parthasarathy, K.; Cheng, C. H. Angew. Chem., Int. Ed. 2012, 51, 197
33. Parthasarathy, K.; Senthilkumar, N.; Jayakumar, J.; Cheng, C. H. Org. Lett. 2012, 14, 3478
34. Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414