A general and efficient method for the synthesis of benzo-(iso)quinoline derivatives

Tetrahedron

Volumn 64, Issue 47, 2008, Pages 10699-10705

  Mamane, Victor ^a   Louërat, Frédéric ^a   Iehl, Julien ^a   Abboud, Mohamed ^a   Fort, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CROSS COUPLING REACTION; CYCLIZATION; PRIORITY JOURNAL; SUZUKI REACTION; SYNTHESIS;

EID: 53149092028     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.015     Document Type: Article

References (52)

1. Atatreh N., Stojkoski C., Smith P., Booker G.W., Dive C., Frenkel A.D., Freeman S., and Bryce R.A. Bioorg. Med. Chem. Lett. 18 (2008) 1217-1222
2. Cappelli A., Giuliani G., Gallelli A., Valenti S., Anzini M., Mennuni L., Makovec F., Cupello A., and Vomero S. Bioorg. Med. Chem. 13 (2005) 3455-3460
3. Murthy M., Pedemonte N., MacVinish L., Malietta L., and Cuthbert A. Eur. J. Pharmacol. 516 (2005) 118-124
4. Szkotak A.J., Murthy M., MacVinish L.J., Duszyk M., and Cuthbert A.W. Br. J. Pharmacol. 142 (2004) 531-542
5. Kerry M.A., Boyd G.W., Mackay S.P., Meth-Cohn O., and Platt L. J. Chem. Soc., Perkin Trans. 1 (1999) 2315-2321
6. Cappelli A., Anzini M., Vomero S., Mennuni L., Makovec F., Doucet E., Hamon M., Bruni G., Romeo M.R., Menziani M.C., De Benedetti P.G., and Langer T. J. Med. Chem. 41 (1998) 728-741
7. Matsumiya H., Hoshino H., and Yotsuyanagi T. Analyst 126 (2001) 2082-2086
8. Chou P.-T., and Wei C.-Y. J. Phys. Chem. 100 (1996) 17059-17066
9. Prema D., Wiznycia A.V., Scott B.M.T., Hilborn J., Desper J., and Levy C.J. Dalton Trans. (2007) 4788-4796
10. Wang X.-S., Li Q., Yao C.-S., and Tu S.-J. Eur. J. Org. Chem. (2008) 3513-3515
11. Wang X.-S., Li Q., Wu J.-R., Li Y.-L., Yao C.-S., and Tu S.-J. Synthesis (2008) 1902-1910
12. Hewlins M.J.E., and Salter R. Synthesis (2007) 2157-2163
13. Li A.-H., Ahmed E., Chen X., Cox M., Crew A.P., Dong H.-Q., Jin M., Ma L., Panicker B., Siu K.W., Steinig A.G., Stolz K.M., Tavares P.A.R., Volk B., Weng Q., Werner D., and Mulvihill M.J. Org. Biomol. Chem. 5 (2007) 61-64
14. Alajarin M., Vidal A., and Ortin M.-M. Tetrahedron 61 (2005) 7613-7621
15. Sangu K., Fuchibe K., and Akiyama T. Org. Lett. 6 (2004) 353-355
16. Mahata P.K., Venkatesh C., Kumar U.K.S., Ila H., and Junjappa H. J. Org. Chem. 68 (2003) 3966-3975
17. Campos P.J., Anon, Malo M.C., Tan C.-Q., and Rodriguez M.A. Tetrahedron 54 (1998) 6929-6938
18. Wrobel Z. Tetrahedron 54 (1998) 2607-2618
19. Riesgo E.C., Jin X., and Thummel R.P. J. Org. Chem. 61 (1996) 3017-3022
20. Collis G.E., and Burrell A.K. Tetrahedron Lett. 46 (2005) 3653-3656
21. Harrowven D.C., Sutton B.J., and Coulton S. Org. Biomol. Chem. 1 (2003) 4047-4057
22. Harrowven D.C., Sutton B.J., and Coulton S. Tetrahedron Lett. 42 (2001) 9061-9064
23. Harrowven D.C., Nunn M.I.T., Blumire N.J., and Fenwick D.R. Tetrahedron 57 (2001) 4447-4454
24. Harrowven D.C., and Nunn M.I.T. Tetrahedron Lett. 39 (1998) 5875-5876
25. Hewlins M.J.E., and Salter R. Synthesis (2007) 2164-2174
26. Lewis F.D., Kalgutkar R.S., and Yang J.-S. J. Am. Chem. Soc. 123 (2001) 3878-3884
27. Aloui F., El Abed R., Marinetti A., and Ben Hassine B. Tetrahedron Lett. 49 (2008) 4092-4095
28. Abbate S., Bazzini C., Caronna T., Fontana F., Gambarotti C., Gangemi F., Longhi G., Mele A., Sora I.N., and Panzeri W. Tetrahedron 62 (2006) 139-148
29. Harrowven D.C., Guy I.L., and Nanson L. Angew. Chem., Int. Ed. 45 (2006) 2242-2245
30. Dix I., Doll C., Hopf H., and Jones P.G. Eur. J. Org. Chem. (2002) 2547-2556
31. Li A., Gilbert T.M., and Klumpp D.A. J. Org. Chem. 73 (2008) 3654-3657
32. Li A., Kindelin P.J., and Klumpp D.A. Org. Lett. 8 (2006) 1233-1236
33. Mamane V., and Fort Y. J. Org. Chem. 70 (2005) 8220-8223
34. Cassity R.P., Taylor L.T., and Wolfe J.F. J. Org. Chem. 43 (1978) 2286-2288
35. Pathak R., Vandayar K., van Otterlo W.A.L., Michael J.P., Fernandes M.A., and de Koning C.B. Org. Biomol. Chem. 2 (2004) 3504-3509
36. de Koning C.B., Michael J.P., Nhlapo J.M., Pathak R., and van Otterlo W.A.L. Synlett (2003) 705-707
37. de Koning C.B., Michael J.P., and Rousseau A. J. Chem. Soc., Perkin Trans. 1 (2000) 1705-1713
38. de Koning C.B., Michael J.P., and Rousseau A. J. Chem. Soc., Perkin Trans. 1 (2000) 787-797
39. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457-2483
40. For the synthesis of compound 1a see:. Pasquinet E., Rocca P., Richalot S., Guéritte F., Guénard D., Godard A., Marsais F., and Quéguiner G. J. Org. Chem. 66 (2001) 2654-2661
41. For the synthesis of compound 1c see:. Spivey A.C., Shukla L., and Hayler J.F. Org. Lett. 9 (2007) 891-894
42. For compounds 1d and 1e see:. Mal P., Lourderaj U., Parveen P., Venugopalan P., Narasimba Moorthy J., and Sathyamurthy N. J. Org. Chem. 68 (2003) 3446-3453
43. For compound 1f see:. Wijtmans M., Pratt D.A., Brinkhorst J., Serwa R., Valgimigli L., Pedulli G.F., and Porter N.A. J. Org. Chem. 69 (2004) 9215-9223
44. The connectivity information was unambiguously established by analysis of NMR data using HMBC technique.
45. Mamane V., Aubert E., and Fort Y. J. Org. Chem. 72 (2007) 7294-7300
46. Mamane V., and Fort Y. Tetrahedron Lett. 47 (2006) 2337-2340
47. Mamane V. Targets in Heterocyclic Systems. In: Attanasi O., and Spinelli D. (Eds). Chemistry and Properties (2006), Società Chimica Italiana (SCI), Urbino, Italy Vol. 10, pp 197-231
48. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 (2002), Wiley-Interscience, New York, NY Part III
49. Abe Y., Ohsawa A., and Igeta H. Heterocycles 19 (1982) 49-51
50. McMillan F.M., McNab H., and Reed D. Tetrahedron Lett. 48 (2007) 2401-2403
51. For metal-catalyzed amination of similar structures see:. Desmarets C., Schneider R., and Fort Y. Tetrahedron Lett. 42 (2001) 247-250
52. For a recent related work in phenanthrene synthesis see:. Kim Y.H., Lee H., Kim Y.J., Kim B.T., and Heo J.-N. J. Org. Chem. 73 (2008) 495-501