New synthesis of 3-aryl isoquinolines by Pd-catalyzed Suzuki cross-coupling

Letters in Organic Chemistry

Volumn 4, Issue 2, 2007, Pages 86-91

  Franceschin, Marco ^a   Frasca, Stefano ^a   Alvino, Antonello ^a   Bianco, Armandodoriano ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

3 aryl isoquinolines; Pd catalysis; Suzuki cross coupling

Indexed keywords

EID: 34247625152     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807780414217     Document Type: Article

References (29)

1. Nakanishi, T.; Suzuki, M. J. Nat. Prod., 1998, 61, 1263.
2. (a) Kanzawa, F.; Nishio, K.; Ishida, T.; Fukuda, M.; Kurokawa, H.; Fukumoto, H.; Nomoto, Y.; Fukuoka, K.; Bojanowski, K.; Saijo, N. Br. J. Cancer, 1997, 76, 571;
3. (b) Nakanishi, T.; Suzuki, M.; Saimoto, A.; Kabasawa, T. J. Nat. Prod., 1999, 62, 864.
4. (a) Jantovà, S. J. Pharm. Pharmacol., 2003, 55, 1143;
5. (b) Franceschin, M.; Rossetti, L.; D'Ambrosio, A.; Schirripa, S.; Bianco, A.; Ortaggi, G.; Savino, M.; Schultes, C.; Neidle, S. Bioorg. Med. Chem. Lett., 2006, 16, 1707.
6. Cho, W.J.; Kim, E.K.; Park, I.Y.; Jeong, E.Y.; Kim, T.S.; Le, T.N.; Kim, D.D.; Lee, E.S. Bioorg. Med. Chem., 2002, 10, 2953.
7. Van MuijIwijk-Koezen, J.F.; Timmerman, H.; van der Goot, H.; Menge, W.M.P.B.; von Drabbe Künzel, J.F.; de Groote, M.; IJzerman, A.P. J. Med. Chem., 2000, 43, 2227.
8. Huang, Q.; Hunter, J.A.; Larock, R.C. Org. Lett., 2001, 3, 2973.
9. Dai, G.; Larock, R.C. J. Org. Chem., 2003, 68, 920.
10. Cho, W.J.; Min, S.Y.; Le, T.N.; Kim, T.S. Bioorg. Med. Chem. Lett., 2003, 13, 4451.
11. Miyaura, N. In Topics in Current Chemistry, Miyaura, N. Ed.; Springer-Verlag, Berlin. 2002; Vol. 219, pp. 11-59.
12. (a) Heck, R.F. Acc. Chem. Res., 1979, 12, 146;
13. (b) Heck, R.F. Org. React. (NY), 1982, 27, 345;
14. (c) Heck, R.F. Palladium Reagents in Organic Synthesis, Academic Press: London, 1985;
15. (d) Bianco, A.; Cavarischia, C.; Guiso, M. Eur. J. Org. Chem., 2004, 2894.
16. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett., 1975, 4467;
17. (b) Franceschin, M.; Alvino, A.; Ortaggi, G.; Bianco, A. Tetrahedron Lett., 2004, 45, 9015.
18. (a) Koyama, T.; Hirota, T.; Shinohara, Y.; Masatoshi, Y.; Ohmori, S. Chem. Pharm. Bull., 1974, 23, 497;
19. (b) Hirota, T.; Koyama, T.; Nanba, T.; Yamato, M. Chem. Pharm. Bull., 1977, 25, 2838.
20. Chaumeil, H.; Signorella, S.; Le Drian, C. Tetrahedron Lett., 2000, 56, 9655.
21. Yin, J.J.; Rainka, M.P.; Zhang, X.X.; Buchwald, S.L. J. Am. Chem. Soc., 2002, 124, 1162.
22. Hesse, S.; Kirch, G. Synthesis, 2001, 755.
23. Miyaura, N.; Suzuki, A. Chem. Rev., 1995, 95, 2457.
24. Smith, G.B.; Dezeny, G.C.; Hughes, D.L.; King, A.O.; Verhoeven, T.R. J. Org. Chem., 1994, 59, 8151.
25. Sheldon, R.A.; Kochi, J.K. Catalyzed Oxidations of Organic Compounds Academic Press, New York, 1981; pp. 79-83.
26. Schomaker, J.M.; Delia, T.J. J. Org. Chem., 2001, 66, 7125.
27. Miyaura, N. Metal-Catalyzed Cross-Coupling Reactions of Organoboron Compounds with Organic Halides in Metal-Catalyzed Cross-Coupling Reactions (2nd edition), de Meijere, A.; Diederich, F. Eds. Wiley-VCH, Weinheim 2004, pp. 41-216.
28. Zoltewicz, J.A.; Cruskie M.P.; Dill, C.D. J. Org. Chem., 1995, 60, 264.
29. Illuminati, G. Adv. Heterocycl. Chem., 1964, 3, 285.