Functionalization by metallation of fluoropyrazine. Diazines XXI

Tetrahedron

Volumn 54, Issue 19, 1998, Pages 4899-4912

  Plé, Nelly ^a   Turck, Alain ^a   Heynderickx, Arnault ^a   Quéguiner, Guy ^a  

^a IRCOF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM; PYRAZINE DERIVATIVE; SULFADIAZINE;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SYNTHESIS; TECHNIQUE;

EID: 0032079610     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00173-2     Document Type: Article

References (26)

1. 1.-Barlin, G.B.; The pyrazines in the chemistry of heterocyclic compounds. A. Weissberger and E. C. Taylors, eds, Interscience, New-york 1982 p.95.
2. 2.-Porter, A. E. A.; Pyrazines and their Benzo Derivatives in Comprehensive Heterocyclic Chemistry, vol. 3, Boulton A. J. and Mc Killop, A.; eds, Pergamon, Oxford, 1984, p. 157.
3. 3.-Turck, A.; Mojovic, L.; Quéguiner, G. Synthesis 1988, 881.
4. 4.-a) Turck, A.; Plé, N.; Quéguiner, G. Heterocycles 1994, 37, 2149.
5. b) Plé, N.; Turck, A.; Heynderickx, A; Quéguiner, G. J. Heterocyclic Chem. 1994, 31, 1311.
6. c) Plé, N.; Turck, A.; Heynderickx, A; Quéguiner, G. J. Heterocyclic Chem. 1997, 34, 551.
7. 5.-a) Chambers, R. D.; Drakesmith, F. G.; Musgrave, W. K. R.; 1965, J. Chem. Soc., 5045.
8. b) Chambers, R. D.; Heaton, C. A.; Musgrave, W. K. R. 1969, J. Chem. Soc. C, 1700
9. c) Marsais, F.; Granger, P.; Quéguiner, G. J Org Chem 1981, 46, 4494.
10. d) Güngor, T.; Marsais, F. Quéguiner, G. J. Organomet. Chem.1979, 171, 273.
11. e) Marsais, F.; Quéguiner, G. Tetrahedron, 1983, 39, 2009.
12. f) Mallet, M.; Quéguiner, G. Tetrahedron, 1979, 35, 1625.
13. g) Mallet, M.; Quéguiner, G. Tetrahedron, 1982, 38, 3035.
14. h) Mallet, M.; Marsais, M.; Branger, G.; Quéguiner, G. J. Organomet. Chem,.1990, 382, 319.
15. 6. - Marsais, F.; Bouley, E.; Quéguiner, G. J. Organomet. Chem. 1979, 171, 273.
16. 7.-a) Rutner, H.; Spoerri, P. E. J. Heterocyclic Chem., 1965, 2, 492.
17. b) Rutner, H.; Spoerri, P. E. J. Heterocyclic Chem., 1966, 3, 435.
18. c) Cheeseman, G. W. H.; Godwin, R.A. J. Chem. Soc. C, 1971, 2973.
19. d) Zergenyi, J.; Raz, B. Eur. Pat. App. EP ,1984, 122,355.
20. e) Yukitaka, U.; Masayuki, U.; Hirosuki, Y. Heterocycles, 1992, 34, 1507.
21. 8.-In the "in situ trapping" method, the substrate to metallate and the electrophile are simultaneously introduced in a solution of metallating agent.
22. 9.-Jovanovic, M. V. Heterocycles, 1984, 22, 1105.
23. 10.-Street, L. J.; Baker, R.; Book, T.; Reeve, A.; Saunders, J. J. Med. Chem., 1992, 35, 295.
24. 11.-Showell, G. A.; Baker, R.; Connollt, S.; Snow, R. J.; Stanfield, I. Med. Chemical. Res.,1993, 171.
25. 12.-Plé, N.; Turck, A.; Couture, K.; Quéguiner, G. Tetrahedron, 1994, 50, 10299.
26. 13.-Bizot, J. Bull Soc. Chem. Fr., 1967, 1, 151.