Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange

Journal of Organic Chemistry

Volumn 65, Issue 15, 2000, Pages 4618-4634

  Abarbri, Mohamed ^a   Thibonnet, Jérôme ^a   Bérillon, Laurent ^a   Dehmel, Florian ^a   Rottländer, Mario ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CHLORINE; HETEROCYCLIC COMPOUND; IODINE; MAGNESIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ION EXCHANGE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034725741     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000235t     Document Type: Article

References (50)

1. (a) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: Weinheim, 1996.
2. (b) Wipf, P.; Venkatraman, S. J. Org. Chem. 1998, 61, 6517.
3. (c) Wipf, P.; Hayes G. B.; Tetrahedron 1998, 54, 6987.
4. (d) Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556.
5. (a) Newkome, G. R.; Pandler, W. W. Contemporary Heterocyclic Chemistry; Wiley: New York, 1982.
6. (b) Gilchrist, T. L. Heterocycl. Chem. VCH: Weinheim, 1995.
7. (c) Boucher, E.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408.
8. (a) Peczuh, M. W.; Hamilton, A. D.; Sánchez-Quesada, J.; de Mendoza, J.; Haack, T.; Giralt, E. J. Am. Chem. Soc. 1997, 119, 9327.
9. (b) Fan, E.; Vicent, C.; Hamilton, A. D. New J. Chem. 1997, 21, 81.
10. (c) Goodman, M. S.; Jubian, V.; Hamilton, A. D. Tetrahedron Lett. 1995, 36, 2551.
11. Ziessel, R. Synthesis 1999, 1839.
12. (a) Snieckus, V. Chem. Rew. 1990, 90, 879.
13. (b) Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49.
14. (c) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron 1993, 49, 9713.
15. Lipshutz, B. H.; Hagen, W. Tetrahedron Lett. 1992, 33, 5865.
16. Burns, T. P.; Rieke, R. D. J. Org. Chem. 1987, 52, 3674.
17. (a) Boymond, L.; Rottländer, M.; Cahiez, G.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1998, 37, 1701.
18. (b) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449.
19. Rottländer, M.; Boymond, L.; Cahiez, G.; Knochel, P. J. Org. Chem. 1999, 64, 1080.
20. (a) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé, N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359.
21. (b) Abarbri, M.; Knochel, P. Synlett 1999, 1577.
22. (c) Dehmel, F.; Abarbri, M.; Knochel, P. Synlett 1999, 345-346.
23. Avolio, S.; Malan, C.; Marek, I.; Knochel, P. Synlett 1999, 11, 1820.
24. (a) Paradies, H. H.; Görbing, H. Angew. Chem., Int. Ed. Engl. 1969, 8, 279.
25. (b) Smith, C. F.; Moore, G. J.; Tamborski, C. J. Organomet. Chem. 1971, 33, 21.
26. (c) Cahiez, G.; Bernard, D.; Normant, J. F. J. Organomet. Chem. 1976, 113, 107.
27. (d) Seyferth, D.; Lambert, R. L. J. Organomet. Chem. 1973, 54, 123.
28. (e) Redwane, N.; Moreau, P.; Commeyras, A. J. Fluorine Chem. 1982, 20, 699.
29. (f) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845.
30. (g) Nishiyama, H.; Isaka, K.; Itoh, K.; Ohno, K.; Nagese, H.; Matsumoto, K.; Yoshiwara, H. J. Org. Chem. 1992, 57, 407.
31. (a) Villiéras, J. Bull. Soc. Chim. Fr. 1967, 1520.
32. (b) Bolm, C.; Pupowicz, D. Tetrahedron Lett. 1997, 38, 7349.
33. Trecourt, F.; Breton, G.; Mongiu, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339.
34. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
35. Millot, N.; Piazza, C.; Avolio, S.; Knochel P. Synthesis 2000, submitted.
36. Goodby, J. W.; Hird, M.; Lewis, R. A.; Toyne, K. J. J. Chem. Soc., Chem. Commun. 1996, 2719.
37. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
38. Schumacher, R. W.; Davidson, B. S. Tetrahedron 1999, 55, 935.
39. Rho, T.; Abuh, Y. F. Synth. Commun. 1994, 24, 253.
40. Almena, J. J. P.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073.
41. Bergman, J.; Venemalm, L. J. Org. Chem. 1992, 57, 2495.
42. (a) Hartly, D. J.; Iddon, B. Tetrahedron Lett. 1997, 38, 4667;
43. (b) O'Connell, J. F.; Parquette, J.; Yelle, W. E.; Wang, W.; Rapoport, H. Synthesis 1988, 767.
44. Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godart, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832.
45. Riley, M.; Perham, R. N. J. Biochem. 1973, 131, 625.
46. Das, B.; Kundu, N. G. Synth. Comm. 1988, 18, 855.
47. Iddon, B.; Lim, B. L. J. Chem. Soc., Perkin Trans. 1983, 735.
48. Fournari, P.; Guilard, R.; Person, M. Bull Soc. Chim. Fr. 1967, 4115.
49. Gilow, H. M.; Burton, D. E. J. Org. Chem. 1981, 46, 2221.
50. Ung, A. T.; Pyne, S. G. Tetrahedron: Asymmetry 1998, 9, 1395.