An expeditious synthesis of 6-aminophenanthridines

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3725-3727

  Gug, Fabienne ^a   Blondel, Marc ^b   Desban, Nathalie ^b   Bouaziz, Serge ^a   Vierfond, Jean Michel ^a   Galons, Hervé ^a  

^a INSERM   (France)

^b CNRS   (France)

Author keywords

Phenanthridine; Prion; Suzuki coupling

Indexed keywords

6 AMINO 8 CHLOROPHENANTHRIDINE; ANILINE DERIVATIVE; BENZONITRILE; BIPHENYL DERIVATIVE; PHENANTHRIDINE DERIVATIVE; PRION PROTEIN; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SUZUKI MYAURA REACTION;

LATEOLABRAX JAPONICUS;

EID: 17844408447     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.135     Document Type: Article

References (25)

1. C. Soto, and J. Castilla Nat. Med. 10 2004 S63 S67
2. S. Bach, N. Talarek, J.-M. Vierfond, Y. Mettey, H. Galons, L. Meijer, C. Cullin, and M. Blondel Nat. Biotechnol. 2003 1075 1081
3. F. Gug, S. Bach, M. Blondel, J.-M. Vierfond, A.-S. Martin, and H. Galons Tetrahedron 60 2004 4705 4708
4. A.J. Suzuki Orgamet. Chem. 576 1999 147 168
5. S. Kotha, L. Kakali, and D. Kashinath Tetrahedron 58 2002 9633 9695
6. F. Bellina, A. Carpita, and R. Rossi Synthesis 2004 2419 2440
7. C.A. Parrish, and S.L. Buchwald J. Org. Chem. 66 2001 3820 3827
8. K. Okamoto, R. Akiyama, and S. Kobayashi Org. Lett. 6 2004 1987 1990
9. L.R. Moore, and K.H. Shaughnessy Org. Lett. 6 2004 225 228
10. O. Navarro, Y. Oonishi, R.A. Kelly, E.D. Stevens, O. Briel, and S.P. Nolan J. Organomet. Chem. 2004 3722 3727
11. F. Berthiol, I. Kondolff, H. Doucet, and M. Santelli J. Organomet. Chem. 689 2004 2786 2798
12. B. Tao, and D.W. Boykin J. Org. Chem. 69 2004 4330 4335
13. B. Tao, and D.W. Boykin Tetrahedron Lett. 44 2003 7993 7996
14. J.-H. Li, and W.-J. Liu Org. Lett. 6 2004 2809 2811
15. I. Özdemir, B. Alici, N. Gürbûz, E. Çetinkaya, and B. Çetinkaya J. Mol. Catal. A 217 2004 37 40
16. M. Gruber, S. Chouzier, K. Koehler, and L. Djakovitch Appl. Catal. A: Gen. 265 2004 161 169
17. Y. Satoh, C. Gude, K. Chan, and F. Firooznia Tetrahedron Lett. 38 1997 7645 7648
18. M. Prieto, E. Zurita, M.L. Rosa, P. Lloyd-Williams, and E. Giralt J. Org. Chem. 69 2004 6812 6820
19. O. Baudouin, M. Cesario, D. Guénard, and F. Guéritte J. Org. Chem. 67 2002 1199 1207
20. The chemistry of functionalised boronic esters have been reviewed: D.S. Matteson J. Organomet. Chem. 581 1999 51 65
21. 3): δ 5.11 (s, 2H); 6.94 (dd, 1H); 7.10 (d, 1H); 7.40 (br s, 5H); 6.55 (d, 1H)
22. 3): 121.3 (1a-C); 122.8 (7a-C); 123 (7-C); 123 (2-C); 126.6 (4-C); 127 (8-C); 127.1 (1-C); 129.7 (3-C); 131.3 (10a-C); 132 (10-C); 135.2 (9-C); 144 (4a-C); 154.0 (6-C)
23. The bulk of the electron-rich ligands is regularly considered to facilitate Suzuki coupling
24. M.A. Siddiqui, and V. Snieckus Tetrahedron Lett. 29 1988 5463 5466
25. J.J.S. Lamba, and J.M. Trost J. Am. Chem. Soc. 116 1994 11723 11736