Synthesis of amino-functionalized 2,2′-bipyridines

Synthesis

Volumn , Issue 17, 2007, Pages 2711-2719

  Hapke, Marko ^b   Staats, Holger ^a   Wallmann, Ivonne ^a   Lützen, Arne ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Amines; Bipyridine; Cross coupling reactions; Palladium; Protecting group

Indexed keywords

BIPYRIDINE; CROSS-COUPLING REACTIONS; PROTECTING GROUP;

CHELATION; LIGANDS; PHASE TRANSITIONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AMINES;

2 BROMO 4 (2,5 DIMETHYL 1H PYRROL 1 YL)PYRIDINE; 2 CHLORO 3 (2,5 DIMETHYL 1H PYRROL 1 YL)PYRIDINE; 2 CHLORO 4 (3,3 DIETHYLTRIAZ 1 EN 1 YL)PYRIDINE; 2 CHLORO 4 [(PYRROLIDIN 1 YL)DIAZENYL]PYRIDINE; 2 CHLORO 6 (2,5 DIMETHYL 1H PYRROL 1 YL)PYRIDINE; 4 (3,3 DIETHYLTRIAZ 1 EN 1 YL) 6' (2,5 DIMETHYL 1H PYRROL 1 YL) 2,2' BIPYRIDINE; 4 (3,3 DIETHYLTRIAZ 1 EN 1 YL) 6' HYDROXY 2,2' BIPYRIDINE; 4,4' BIS(2,5 DIMETHYL 1H PYRROL 1 YL) 2,2' BIPYRIDINE; 4,4' DIAMINO 2,2' BIPYRIDINE; 4,5' DIAMINO 2,2' BIPYRIDINE; 4,6' BIS(2,5 DIMETHYL 1H PYRROL 1 YL) 2,2' BIPYRIDINE; 4,6' BIS(ACETYLAMINO) 2,2' BIPYRIDINE; 4,6' DIBROMO 2,2' BIPYRIDINE; 4,6' DIIODO 2,2' BIPYRIDINE; 5,5' BIS(2,5 DIMETHYL 1H PYRROL 1 YL) 2,2' BIPYRIDINE; 5,6' BIS(2,5 DIMETHYL 1H PYRROL 1 YL) 2,2' BIPYRIDINE; 5,6' DIAMINO 2,2' BIPYRIDINE; 6 (2,5 DIMETHYL 1H PYRROL 1 YL) 4' [(PYRROLIDIN 1 YL)DIAZENYL] 2,2' BIPYRIDINE; 6 AMINO 4 (3,3 DIETHYLTRIAZ 1 EN 1 YL) 2,2' BIPYRIDINE; 6 METHOXY 4' [(PYRROLIDIN 1 YL)DIAZENYL] 2,2' BIPYRIDINE; 6,6' BIS(2,5 DIMETHYL 1H PYRROL 1 YL) 2,2' BIPYRIDINE; 6,6' DIAMINO 2,2' BIPYRIDINE; BIPYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CROSS COUPLING REACTION; SYNTHESIS;

EID: 34548698680     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983824     Document Type: Article

References (37)

1. Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.
2. For the synthetic introduction of the bipyridine core in the synthesis of caerulomycin C, see: Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. In Strategies and Tactics in Organic Synthesis, Vol. 6; Harmata, M., Ed.; Elsevier: New York, 2005, 415.
3. Newkome, G. R.; Petri, A. K.; Holder, E.; Schubert, U. S. Eur. J. Org. Chem. 2004, 235.
4. (a) Lützen, A.; Hapke, M. Eur. J. Org. Chem. 2002, 2292.
5. (b) Lützen, A.; Hapke, M.; Staats, H.; Bunzen, J. Eur. J. Org. Chem. 2003, 3948.
6. (c) Kiehne, U.; Bunzen, J.; Staats, H.; Lützen, A. Synthesis 2007, 1061.
7. Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000.
8. Examples: (a) Whittle, C. P. J. Heterocycl. Chem. 1977, 14, 191.
9. (b) Newkome, G. R.; Gross, J.; Patri, A. K. J. Org. Chem. 1997, 62, 3013.
10. (c) Zhang, B.; Breslow, R. J. Am. Chem. Soc. 1997, 119, 1676.
11. (d) Thibault, M. E.; Luska, K. L.; Schlaf, M. Synthesis 2007, 791.
12. Albrecht, M.; Janser, I.; Lützen, A.; Hapke, M.; Fröhlich, R.; Weis, P. Chem. Eur. J. 2005, 11, 5742.
13. Some recent examples for the use of LiCl as an additive in organometallic mediated reactions: (a) Krasovskiy, A.; Knochel, P. Angew. Chem. Int. Ed. 2004, 43, 3333;
14. Angew. Chem. 2004, 116, 3396.
15. (b) Krasovskiy, A.; Straub, B.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 159;
16. Angew. Chem. 2006, 118, 165.
17. (c)Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 2958;
18. Angew. Chem. 2006, 118, 3024.
19. (d) Krasovskiy, A.; Tishkov, A.; del Amo, V.; Mayr, H.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 5010;
20. Angew. Chem. 2006, 118, 5132.
21. (e) Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 6040;
22. Angew. Chem. 2006, 118, 6186.
23. (f) del Amo, V.; Dubbaka, S. R.; Krasovskiy, A.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 7838;
24. Angew. Chem. 2006, 118, 8002.
25. (g) Korn, T. B.; Scahde, M. A.; Cheemala, M. N.; Wirth, S.; Guevara, S. A.; Cahiez, G.; Knochel, P. Synthesis 2006, 3547.
26. (h) Kloetzing, R. J.; Krasovskiy, A.; Knochel, P. Chem. Eur. J. 2007, 13, 215.
27. Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80.
28. Examples: (a) Janiak, C.; Deblon, S.; Wu, H.-P.; Kolm, M. J.; Klufers, P.; Piotrowski, H.; Mayer, P. Eur. J. Inorg. Chem. 1999, 1507.
29. (b) Devic, T.; Avarvari, N.; Batail, P. Chem. Eur. J. 2004, 10, 3697.
30. (c) Ishida, H.; Kyakuno, M.; Oishi, S. Biopolymers 2004, 76, 69.
31. General overview: Schelhaas, M.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2056;
32. Angew. Chem. 1996, 108, 2192.
33. Bräse, S. Acc. Chem. Res. 2004, 37, 805.
34. Conditions: Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R. Synthesis 2001, 2180.
35. Suffert, J. J. Org. Chem. 1989, 54, 509.
36. Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
37. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer Verlag: Berlin, 1999, 2.