Nickel-mediated amination chemistry. Part 2: Selective N-arylation or N,N'-diarylation of piperazine

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2881-2884

  Brenner, Eric ^a   Schneider, Raphaël ^a   Fort, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

Arylamination; N,N' diarylpiperazine; N arylpiperazine; Nickel

Indexed keywords

NICKEL; PIPERAZINE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; LIGAND BINDING; PROTEIN SYNTHESIS INHIBITION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0034655783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00277-X     Document Type: Article

References (37)

1. (a) Mokrosz, J. L.; Pietrasiewicz, M.; Duszunska, B.; Cegla, M. T. J. Med. Chem. 1992, 35, 2369.
2. (b) Perez, M.; Fourrier, C.; Sigogneau, I.; Pauwels, P. J.; Palmier, C.; John, G. W.; Valentin, J. P.; Halazy, S. J. Med. Chem. 1995, 38, 3602.
3. (c) Broekkamp, C. L. E.; Leysen, D.; Peeters, B. W. M. M.; Pinder, R. M. J. Med. Chem. 1995, 38, 4615.
4. (d) Lopez-Rodriguez, M. L.; Morcillo, M. J.; Fernandez, E.; Porras, E.; Murcia, M.; Sanz, A. M.; Orensanz, L. J. Med. Chem. 1997, 40, 2653.
5. (e) Lopez-Rodriguez, M. L.; Morcillo, M. J.; Fernandez, E.; Rosado, M. L.; Orensanz, L.; Beneytez, M. E.; Manzanares, J.; Fuentes, J. A.; Schaper, K. J. Bioorg. Med. Chem. Lett. 1999, 9, 1679.
6. (f) Lopez-Rodriguez, M. L.; Viso, A.; Benhamu, B.; Rominguera, J. L.; Murcia, M. Bioorg. Med. Chem. Lett. 1999, 9, 2339.
7. (a) Hepperle, M.; Eckart, J.; Gala, D. Tetrahedron Lett. 1999, 40, 5655.
8. (b) Tanoury, G. T.; Senenayaka, C. H.; Hett, R.; Kuhn, A. M.; Kessler, D. W.; Wald, S. A. Tetrahedron Lett. 1998, 39, 6845.
9. Hagibara, M.; Kashiwase, H.; Katsube, T.; Kimura, T.; Komai, T.; Momota, K.; Ohmine, T.; Nishigaki, T.; Kimura, S.; Shimada, K. Bioorg. Med. Chem. Lett. 1999, 9, 3063.
10. Xia, Y.; Mirzai, B.; Chackamannil, S.; Czarniecki, M.; Wang, S.; Clemmons, A.; Ahn, H.-S.; Boykow, G. C. Bioorg. Med. Chem. Lett. 1996, 6, 919.
11. (a) Ten Hoeve, W.; Kruse, C. G.; Luteyn, J. M.; Thiecke, J. R. G.; Wynberg, H. J. Org. Chem. 1993, 58, 5101.
12. (b) Neuville, L.; Zhu, J. Tetrahedron Lett. 1997, 38, 4091.
13. (c) Hepperle, M.; Eckert, J.; Gala, D. Tetrahedron Lett. 1999, 40, 5655.
14. (a) Dankwardt, S. M.; Newman, S. R.; Krstenansky, J. L. Tetrahedron Lett. 1995, 36, 4923.
15. (b) Pan, P. C.; Sun, C. M. Tetrahedron Lett. 1998, 39, 9505.
16. Perez, M.; Potier, P.; Halazy, S. Tetrahedron Lett. 1996, 37, 8487.
17. (a) Pearson, A. J.; Gelormini, A. M.; Fox, M. A.; Watkins, D. J. Org. Chem. 1996, 61, 1297.
18. (b) Pearson, A. J.; Gelormini, A. M. Tetrahedron Lett. 1997, 38, 5123.
19. Mishani, E.; Dence, C. S.; McCarthy, T. T.; Welch, M. J. Tetrahedron Lett. 1996, 37, 319.
20. (a) Zhao, S.-H.; Miller, A. K.; Berger, J.; Flippin, L. A. Tetrahedron Lett. 1996, 37, 4463.
21. (b) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807.
22. (c) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
23. (d) Witulski, B.; Senft, S.; Thum, A. Synlett 1998, 504.
24. (e) Tanoury, G. J.; Senanayake, C. H.; Hett, R.; Kuhn, A. M.; Kessler, D. W.; Wald, S. A. Tetrahedron Lett. 1998, 39, 6845.
25. (f) Morita, S.; Kitano, K.; Matsubara, J.; Ohtani, T.; Kawano, Y.; Otsubo, K.; Uchida, M. Tetrahedron 1998, 54, 4811.
26. (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046 and references cited therein.
27. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805 and references cited therein.
28. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852 and references cited therein.
29. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125 and references cited therein.
30. (e) Belfield, A. J.; Brown, G. R.; Foubister, A. J. Tetrahedron 1999, 55, 11399 and references cited therein.
31. (f) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
32. (g) Harris, M. C.; Geis, O.; Buchwald, S. L. J. Org. Chem. 1999, 64, 6019.
33. Kerrigan, F.; Martin, C.; Thomas, G. H. Tetrahedron Lett. 1998, 39, 2219.
34. (a) Brenner, E.; Fort, Y. Tetrahedron Lett. 1998, 39, 5359.
35. (b) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
36. -1): 3292 (NH).
37. Pollard, C. B.; MacDowell, L. G. J. Am. Chem. Soc. 1934, 2199.