Pyridylmagnesium chlorides from bromo and dibromopyridines by bromine- magnesium exchange: A convenient access to functionalized pyridines

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4339-4342

  Trécourt, François ^a   Breton, Gilles ^a   Bonnet, Véronique ^a   Mongin, Florence ^a   Marsais, Francis ^a   Quéguiner, Guy ^a  

^a IRCOF   (France)

Author keywords

Exchange reaction; Grignard reagents; Pyridine; Regioselection

Indexed keywords

BROMINE; MAGNESIUM; MAGNESIUM CHLORIDE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION;

EID: 0033522827     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00789-3     Document Type: Article

References (35)

1. (a) Quéguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Adv. Heterocycl. Chem. 1992, 52, 187-304;
2. (b) Godard, A.; Marsais, F.; Plé, N.; Trécourt, F.; Turck, A.; Quéguiner, G. Heterocycles 1995, 40, 1055-1091;
3. (c) Trécourt, F.; Gervais, B.; Mongin, O.; Le Gal, C.; Mongin, F.; Quéguiner, G. J. Org. Chem. 1998, 63, 2892-2897;
4. Pasquinet, E.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1998, 54, 8771-8772.
5. (a) Cai, D.; Hughes, D.L.; Verhoeven, T.R. Tetrahedron Lett. 1996, 35, 2537-2540;
6. (b) Gilman, H.; Spatz, S.M. J Org. Chem. 1951, 16, 1485-1494;
7. (c) Mallet, M.; Branger, G.; Marsais, F.; Quéguiner, G. J. Organomet. Chem. 1990, 382, 319-332.
8. Trécourt, F.; Gervais, B.; Mallet, M.; Quéguiner, G. J. Org. Chem. 1996, 61, 1673-1676.
9. Lai, Y.-H. Synthesis 1981, 585-604.
10. (a) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845-5848;
11. (b) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knöchel, P. Synlett 1998, 1359-1360.
12. Paradies, H.H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem. Int. Ed. Engl. 1969, 8, 279; Paradies, H.H. Naturwissenschaften 1974, 61, 168.
13. Paradies, H.H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem. Int. Ed. Engl. 1969, 8, 279; Paradies, H.H. Naturwissenschaften 1974, 61, 168.
14. Paradies, H.H.; Görbing, M. Angew. Chem. 1969, 81, 293; Angew. Chem. Int. Ed. Engl. 1969, 8, 279; Paradies, H.H. Naturwissenschaften 1974, 61, 168.
15. Martin, G.J.; Mechin, B.; Leroux, Y.; Paulmier, CI.; Meunier, J.C. J. Organomet. Chem. 1974, 67, 327-339.
16. 16
17. Furneaux, R.H.; Limberg, G.; Tyler, P.C.; Schramm, V.L. Tetrahedron 1997, 53, 2915-2930; Gilman, H.; Gregory, W.A.; Spatz, S.M. J. Org. Chem. 1951, 16, 1788-1791.
18. Furneaux, R.H.; Limberg, G.; Tyler, P.C.; Schramm, V.L. Tetrahedron 1997, 53, 2915-2930; Gilman, H.; Gregory, W.A.; Spatz, S.M. J. Org. Chem. 1951, 16, 1788-1791.
19. (a) Bodalski, R.; Katritzky, A.R. J. Chem. Soc. B 1968, 831-838;
20. (b) Buu-Hoï, N.P.; Jacquignon, P.; Rose, A.; Sabathier, J.F.; Sinh, M.P. J. Chem. Soc. 1963, 4269-4271;
21. (c) Hawkins, E.G.E. J. Chem. Soc., Perkin Trans, 1 1972, 2882-2884;
22. (d) Becker, S.; Fort, Y.; Vanderesse, R.; Caubère, P. J. Org. Chem. 1989, 54, 4848-4853;
23. (e) Baker, B.R.; McEvoy, F.J. J. Org. Chem. 1955, 20, 118-142;
24. (f) Adkins, H.; Elofson, R.M.; Rossow, A.G.; Robinson, C.C. J. Am. Chem. Soc. 1949, 71, 3622-3629;
25. (g) Freifelder, M. J. Org. Chem. 1964, 29, 2895-2898;
26. (h) Sauter, F.; Stanetty, P.; Sittenthaler, W.; Waditschatka, R. Monatsh. Chem. 1988, 119, 1427-1438;
27. (i) French, H.E.; Sears, K. J. Am. Chem. Soc. 1951, 73, 469-470;
28. (j) Albert, A.; Barlin, G.B. J. Chem. Soc. 1959, 2384-2396;
29. (k) Brown, H.C.; McDaniel, D.H. J. Am. Chem. Soc. 1955, 77, 3752-3755.
30. Traynelis, V.J.; Gallagher, A.J. J. Org. Chem. 1970, 35, 2792-2796.
31. 3 at 200 MHz): 8.21 (s, 1H), 8.20 (s, 1H), 7.90 (s, 1H), 7.2 (m, 5H, Ph), 5.94 (s, 1H, OH), 5.66 (s, 1H).
32. 3 at 200 MHz): 8.50 (s, 2H), 7.90 (s, 1H), 7.3 (m, 10H, Ph), 6.25 (d, 2H, OH, J= 3.1), 5.85 (d, 2H, J= 3.1).
33. Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T.J. Chem. Soc., Perkin Trans. 1 1996, 1781-1782.
34. Parham, W.E.; Piccirilli, R.M. J. Org. Chem. 1977, 42, 257-260.
35. Streef, J.W.; den Hertog, H.J. Recl. Trav. Chim. Pays-Bas 1966, 85, 803-816.