Metal-halogen exchange using tri-n-butyl lithium magnesate in the diazine series: Diazine 49

Synlett

Volumn , Issue 10, 2006, Pages 1586-1588

  Buron, Frédéric ^a   Plé, Nelly ^a   Turck, Alain ^a   Marsais, Francis ^a  

^a IRCOF   (France)

Author keywords

Ate complex; Diazines; Iodine; Lithium; Magnesium

Indexed keywords

2 BROMOPYRAZINE; 2 CHLOROPYRAZINE; 2 IODOPYRAZINE; 2 METHYLSULFANYL 4 IODOPYRIMIDINE; 3 IODO 6 PHENYLPYRIZADINE; ALCOHOL; ALDEHYDE; BENZENE DERIVATIVE; BENZOPHENONE; DIPHENYLSULFUR; HALOGEN; IODINE; IODINE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM TRI N TRIBUTYLMAGNESATE; MAGNESIUM; METAL; PHENYLSUFANYL; PYRAZINE DERIVATIVE; PYRIMIDINE DERIVATIVE; SULFADIAZINE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; METAL HALOGEN EXCHANGE REACTION; SUBSTITUTION REACTION;

EID: 33745683789     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-941580     Document Type: Article

References (35)

1. (a) Turck, A.; Plé, N.; Mongin, F.; Queguiner, G. Tetrahedron 2001, 57, 4489.
2. (b) Turck, A.; Plé, N.; Queguiner, G. Heterocycles 1994, 37, 2149.
3. (a) Parkanyi, C.; Cho, N. S.; Yoo, G. S. J. Organometal. Chem. 1988, 342, 1.
4. (b) Friseen, A. E.; Marcelis, A. T. M.; Buurman, C. A.; Pollmann, C. A. M.; Van der Plas, H. C. Tetrahedron 1989, 45, 5611.
5. (c) Langley, B. W. J. Am. Chem. Soc. 1956, 78, 2136.
6. (d) Ulbricht, B. W. J. Am. Chem. Soc. 1959, 6, 225.
7. (e) Arai, I.; Daves, G. D. J. Chem. Soc., Chem. Commun. 1976, 69.
8. (f) Strekowski, L. Roczniki Chemii 1975, 49, 1643.
9. (g) Brown, D.; Ogden, R. C. J. Chem. Soc., Perkin Trans. 1 1981, 723.
10. (h) Strekowski, L.; Watson, R. J. Org. Chem. 1986, 51, 3226.
11. (i) Yokoyama, M.; Ikene, T.; Ochiai, Y.; Momotake, A.; Yamaguchi, K.; Togo, H. J. Chem. Soc., Perkin Trans. 1 1998, 2185.
12. (j) Yokoyama, M.; Ikenogami, T.; Togo, H. J. Chem. Soc., Perkin Trans. 1 2000, 2067.
13. (k) Hanessian, S.; Machaalani, R. Tetrahedron Lett. 2003, 44, 8321.
14. von Angerer, S. In Science of Synthesis, Vol. 16; Black, D. St. C., Ed.; Thieme: Stuttgart, 2004, 379.
15. (m) Rajkumar, T. V.; Binkley, S. B. J. Med. Chem. 1963, 6, 550.
16. (a) Hirschberg, A.; Peterkofsky, A.; Spoerri, P. E. J. Heterocycl. Chem. 1965, 2, 209.
17. (b) Hertz, H. S.; Kabacinski, F. F.; Spoerri, P. E. J. Heterocycl. Chem. 1969, 6, 239.
18. (c) Baker, R.; Street, L. J.; Reeve, A. J.; Saunders, J. J. Chem. Soc., Chem. Commun. 1991, 760.
19. (d) Sato, N. In Science of Synthesis, Vol. 16; Black, D. St. C., Ed.; Thieme: Stuttgart, 2004, 751.
20. th National Meeting of the American Chemical Society, Philadelphia, 2004; American Chemical Society: Washington DC, 2004.
21. (f) Street, L. J.; Baker, R.; Book, T.; Reeve, A. J.; Saunders, J.; Willson, T.; Marwood, R. S.; Patel, S.; Freedman, S. J. Med. Chem. 1992, 35, 295.
22. (a) Ple, N.; Turck, A.; Couture, K. Tetrahedron 1994, 50, 10299.
23. (b) Toudic, F.; Ple, N.; Turck, A.; Queguiner, G. Tetrahedron 2002, 58, 283.
24. (a) Abarbri, M.; Knochel, P. Synlett 1999, 1577.
25. (b) Leprêtre, A.; Turck, A.; Ple, N.; Knochel, P.; Queguiner, G. Tetrahedron 1999, 56, 265.
26. (c) Momotake, A.; Mito, J.; Yamaguchi, K.; Togo, H.; Yokoyama, M. J. Org. Chem. 1998, 63, 7207.
27. (d) Shimura, A.; Momotake, A.; Togo, H.; Yokoyama, M. Synthesis 1999, 495.
28. (e) Momotake, A.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1999, 1193.
29. (a) Dumouchel, S.; Mongin, F.; Trécourt, F.; Queguiner, G. Tetrahedron 2003, 59, 8629.
30. (b) Dumouchel, S.; Mongin, F.; Trécourt, F.; Queguiner, G. Tetrahedron Lett. 2003, 44, 2033.
31. (a) Hirschberg, A.; Spoerri, P. E. J. Org. Chem. 1961, 26, 1907.
32. (b) Street, L. J.; Baker, R.; Book, T.; Reeve, A.; Saunders, J. J. Med. Chem. 1992, 35, 295.
33. (c) Majeed, A. J.; Antonsen, O.; Benneche, T.; Undheim, K. Tetrahedron 1989, 45, 993.
34. 2S (262.33): C, 59.52; H, 5.38; N, 10.68. Found: C, 59.34; H, 5.42; N, 10.75.
35. 2 (292.34): C, 73.96; H, 5.52; N, 9.58. Found: C, 73.68; H, 5.48; N, 9.32.