A cascade process toward the synthesis of fused polycyclic dihydropyridines

Tetrahedron Letters

Volumn 47, Issue 14, 2006, Pages 2337-2340

  Mamane, Victor ^a   Fort, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

Cascade reaction; Dihydropyridines; Polycyclic compounds; Suzuki coupling

Indexed keywords

EID: 33644764105     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.010     Document Type: Article

References (27)

1. G. Chelucci, and R. Thummel Chem. Rev. 102 2002 3129
2. C. Kaes, A. Katz, and M.W. Hosseini Chem. Rev. 100 2000 3553
3. V. Balzani, A. Juris, and M. Venturi Chem. Rev. 98 1996 759
4. J.P. Michael Nat. Prod. Rep. 22 2005 627
5. W.A. Denny, and B.C. Baguley Curr. Top. Med. Chem. 3 2003 339
6. A. Padwa Pure Appl. Chem. 75 2003 47
7. V. Mamane, and Y. Fort J. Org. Chem. 70 2005 8220
8. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
9. Y. Abe, A. Ohsawa, and H. Igeta Heterocycles 19 1982 49
10. D.L. Comins, S.P. Joseph, and Y.-M. Zhang Tetrahedron Lett. 37 1996 793
11. D.L. Comins, and Y.-M. Zhang J. Am. Chem. Soc. 118 1996 12248
12. F. Marion, C. Courillon, and M. Malacria Org. Lett. 5 2003 5095
13. A. Alsarabi, J.-L. Canet, and Y. Troin Tetrahedron Lett. 45 2004 9003
14. 1H NMR of the crude mixture showed the presence of the starting material as the major product along with a lot of degradation products. These degradation products were also observed in the crude mixture of entry 1, Table 1. This undesired material could provide from the isomerization of 3 to the other regioisomers and from the oxidation to the pyridinium species.
15. 11NO (233.26): C, 82.38; H, 4.75; N, 6.00. Found: C, 81.87; H, 4.78; N, 5.97. For analytical data of all other compounds, see Supplementary data.
16. J.D. Reinheimer, L.L. Mayle, and G.G. Dolnikowski J. Org. Chem. 45 1980 3097
17. Y. Ishihara, Y. Kiyota, and G. Goto Chem. Pharm. Bull. 38 1990 3024
18. Z. Sui, J. Altom, V.N. Nguyen, J. Fernadez, J.I. Bernstein, J.J. Hiliard, J.F. Barrett, B.L. Podlogar, and K.A. Ohemeng Bioorg. Med. Chem. 6 1998 735
19. R. Alonso, D. Castedo, and D. Dominguez Tetrahedron Lett. 26 1985 2925
20. F.I. Zubkov, E.V. Bolthukina, K.F. Turchin, R.S. Borisov, and A.V. Varlamov Tetrahedron 61 2005 4099
21. W. Zhang, A. Zheng, Z. Liu, L. Yang, and Z. Liu Tetrahedron Lett. 46 2005 5691
22. J. Epsztajn, A. Jozwiak, P. Koluda, I. Sadokierska, and I.D. Wilkowska Tetrahedron 56 2000 4837
23. Y. Yamamoto, K. Kinpara, T. Saigoku, and H. Nishiyama Org. Biomol. Chem. 2 2004 1287
24. I. Osante, E. Lete, and N. Sotomayor Tetrahedron Lett. 45 2004 1253
25. A.R. Katritzki, S. Mehta, and H.-Y. He J. Org. Chem. 66 2001 148
26. A. Moreau, A. Couture, E. Deniau, and P. Grandluchon Eur. J. Org. Chem. 2005 3437
27. A. Moreau, A. Couture, E. Deniau, P. Grandclaudon, and S. Lebrun Tetrahedron 60 2004 6169