First functionalization by metallation of the pyridine moiety of 4-methoxypyridopyrimidines. Diazines: Part 38

Tetrahedron

Volumn 60, Issue 30, 2004, Pages 6353-6362

  Audoux, Jérôme ^a   Plé, Nelly ^a   Turck, Alain ^a   Quéguiner, Guy ^a  

^a Institut de Recherche en Chimie Organique Fine   (France)

Author keywords

Functionalization; Metallation; Methoxypyridopyrimidines

Indexed keywords

PYRIDINE; PYRIMIDINE; SULFADIAZINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LITHIATION; METALLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 3242756767     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.061     Document Type: Article

References (30)

1. Huber B.S., Valenti B.F. J. Med. Chem. 11:1968;708
2. Althius T.H., Moore P.F., Hess H.-J. J. Med. Chem. 22:1979;44
3. Althius T.H., Kadin S.B., Czuba L.J., Moore P.F., Hess H.-J. J. Med. Chem. 23:1980;262
4. Noda, K.; Nakagawa, A.; Motomura, T.; Miyata, S.; Ide, H. Jpn. Patent 50/82094 [75/82094], 1975; Chem. Abstr. 1975, 83, 193376x.
5. (b) Noda, K.; Nakagawa, A.; Nakashima, Y.; Ide, H. Ger. Patent DE 2446323, 1975; Chem. Abstr. 1975, 83, 43375g.
6. (c) Noda, K.; Nakagawa, A.; Motomura, T.; Yamagata, K.; Yamasaki, S.; Miyata, S.; Ide, H. Jpn. Patent 50/140490 [75/140490], 1975; Chem. Abstr. 1976, 85, 21425n.
7. (d) Noda, K.; Nakagawa, A.; Motomura, T.; Yamagata, K.; Miyata, S.; Yamasaki, S.; Nakajima, Y.; Ishikura, Y.; Noguchi, K. Jpn. Patent 50/157394 575/157394], 1975; Chem. Abstr. 1976, 85, 5674n.
8. Cowart M., Lee C. Boiorg. Med. Chem. Lett. 11:2001;83-86
9. Rosowsky A., Chen H. J. Org. Chem. 66:2001;7522-7526
10. Beckwith, A. L. J. US Patent US 3947416, 1976; Chem. Abstr. 1976, 85, 33073j.
11. (b) Kihara, N.; Tomino, I.; Takei, M. Jpn. Patent 61/76488 A2 [76488], 1986; Chem. Abstr. 1986, 105, 208915w.
12. Turck A., Plé N., Tallon V., Quéguiner G. Tetrahedron. 51:1995;13045
13. Plé N., Turck A., Chapoulaud V., Quéguiner G. Tetrahedron. 53:1997;2871-2890
14. Gautheron-Chapoulaud V., Salliot I., Plé N., Turck A., Quéguiner G. Tetrahedron. 55:1999;5389-5404
15. Audoux, J.; Plé, N.; Turck, A.; Quéguiner, G. Submitted for publication.
16. Jastrzebski J.T.B.H., Knaap C.T., Van Koten G. J. Organomet. Chem. 255:1983;287
17. Menon S.C., Singh H.B., Jasinski J.M., Jasinki J.P., Butcher R.J. Organometallics. 15:1996;1707
18. Clayden J., Weslund N., Wilson F.X. Tetrahedron Lett. 40:1999;7883
19. Shirley D.A., Cheng C.F. J. Organomet. Chem. 20:1969;251
20. Sugimoto O., Yamauchi Y., Tanji K.I. Heterocycles. 57:2002;323
21. Plé N., Turck A., Chapoulaud V., Quéguiner G. Tetrahedron. 53:1997;2871
22. Armarego W.L.F. Fused Pyrimidines, Part 1, Quinazoline, Chemistry of Heterocyclic Compounds. 1967;Wiley, New York
23. Murray T.P., Hay J.V., Portlock D.E., Wolfe J.F. J. Org. Chem. 39:1974;595
24. Rathman T.L., Sleevi M.C., Krafft M.K., Wolfe J.F. J. Org. Chem. 45:1980;2169
25. Srinivasan A., Broom A.D. J. Org. Chem. 44:1979;435
26. Anderson G.L., Shim J.L., Broom A.D. J. Org. Chem. 42:1977;993
27. Oakes V., Rydon H.N. J. Chem. Soc. 1956;4433
28. Oakes V., Rydon H.N., Undheim K. J. Chem. Soc. 1962;4678
29. (e) Oakes, V.; Rydon., H. N. U.S. Patent No 2,924,599, 1960; Chem. Abstr. 1960, 54, 9964.
30. Plé N., Turck A., Couture K., Quéguiner G. Tetrahedron. 50:1994;10299