Synthesis of nitro N,N′-dipyridinylamines via oxidative nucleophilic substitution of hydrogen

Synthesis

Volumn , Issue 24, 2007, Pages 3868-3876

  Patriciu, Oana Irina ^a,b,c   Pillard, Christelle ^a   Fînaru, Adriana Luminiţa ^b   Sǎndulescu, Ioan ^c   Guillaumet, Gérald ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b VASILE ALECSANDRI UNIVERSITY OF BACAU   (Romania)

^c UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

Amination; Heterocycles; Nucleophilic aromatic substitution; Palladium; Pyridines

Indexed keywords

AMIDES; AMINATION; HYDROGEN; OPTIMIZATION; PALLADIUM; PYRIDINE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AMINOPYRIDINE DERIVATIVES; HETEROCYCLES; NUCLEOPHILIC AROMATIC SUBSTITUTION;

AMINES;

AMINOPYRIDINE DERIVATIVE; N (3 BROMOPYRIDIN 2 YL) N (5 NITROPYRIDIN 2 YL)AMINE; N (3 BROMOPYRIDIN 2 YL) N (6 CHLORO 5 NITROPYRIDIN 2 YL) N METHYLAMINE; N (3 BROMOPYRIDIN 2 YL) N BUTYL N (5 NITROPYRIDIN 2 YL)AMINE; N (3 BROMOPYRIDIN 2 YL) N METHYL N (5 NITROPYRIDIN 2 YL)AMINE; N (4 METHOXYBENZYL) N (5 NITROPYRIDIN 2 YL) N (PYRIDIN 2 YL)AMINE; N (5 NITROPYRIDIN 2 YL) N (PYRIDIN 2 YL)AMINE; N (6 CHLORO 5 NITROPYRIDIN 2 YL) N (4 METHOXYBENZYL) N (PYRIDIN 2 YL)AMINE; N (6 CHLORO 5 NITROPYRIDIN 2 YL) N (PYRIDIN 2 YL)AMINE; N 2,N 6 BIS(3 BROMOPYRIDIN 2 YL) N 2,N 6 DIMETHYL 3 NITROPYRIDINE 2,6 DIAMINE; N 2,N 6 BIS(4 METHOXYBENZYL) 3 NITRO N 2,N 6 DIPYRIDIN 2 YLPYRIDINE 2,6 DIAMINE; N 2,N 6 BUTYL 3 NITRO N 2,N 6 DIPYRIDIN 2 YLPYRIDINE 2,6 DIAMINE; N 2,N 6 DIMETHYL 3 NITRO N 2,N 6 DIPYRIDIN 2 YLPYRIDINE 2,6 DIAMINE; N BUTYL N (5 NITROPYRIDIN 2 YL) N (PYRIDIN 2 YL)AMINE; N BUTYL N (6 CHLORO 5 NITROPYRIDIN 2 YL) N (PYRIDIN 2 YL)AMINE; N METHYL N (5 NITROPYRIDIN 2 YL) N (PYRIDIN 2 YL)AMINE; N METHYL N (5 NITROPYRIDIN 2 YL) N (PYRIDIN 3 YL)AMINE; N METHYL N (5 NITROPYRIDIN 2 YL) N (PYRIDIN 4 YL)AMINE; N METHYL N (6 CHLORO 5 NITROPYRIDIN 2 YL) N (PYRIDIN 2 YL)AMINE; N,N' DIPYRIDINYLAMINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 37549000522     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990896     Document Type: Article

References (48)

1. (a) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
2. (b) Pinder, A. R. Nat. Prod. Rep. 1992, 9, 491.
3. (c) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581.
4. (d) Brody, F.; Ruby, P. R. Pyridine and Its Derivatives. Part 1. Synthetic and Natural Sources of the Pyridine Ring; Interscience: New York, 1960.
5. (a) Quintela, J. M.; Peinador, C.; González, L.; Iglesias, R.; Paramá, A.; Alvarez, F.; Sanmartin, M. L.; Riguera, R. Eur. J. Med. Chem. 2003, 38, 265.
6. (b) Van Rhee, A. M.; Jiang, J.; Melman, N.; Olah, M. E.; Stiles, G. L.; Jacobson, K. A. J. Med. Chem. 1996, 39, 2980.
7. (c) Bever, C. T. Jr. CNS Drug Rev. 1995, 1, 261.
8. (d) Thomas, G. Medicinal Chemistry; Wiley-VCH: Weinheim, 2002.
9. (e) Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 3rd ed.; Thieme: Stuttgart, 1999,
10. Balboni, G.; Marastoni, M.; Merighi, S.; Borea, P. A.; Tomatis, R. Eur. J. Med. Chem. 2000, 35, 979.
11. Chen, B.-C.; Hynes, J. Jr.; Pandit, C. R.; Zhao, R. Heterocycles 2001, 55, 951.
12. Gfesser, G. A.; Bayburt, E. K.; Cowart, M.; DiDomenico, S.; Gomtsyan, A.; Lee, C.-H.; Stewart, A. O.; Jarvis, M. F.; Kowaluk, E. A.; Bhagwat, S. S. Eur. J. Med. Chem. 2003, 38, 245.
13. Brodbeck, B.; Püllmann, B.; Schmitt, S.; Nettekoven, M. Tetrahedron Lett. 2003, 44, 1675.
14. (a) Terrier, F. Nucleophilic Aromatic Displacement; Verlag Chemie: Weinheim, 1991.
15. (b) Chupakhin, O. N.; Chaushin, V. N.; van der Pias, H. C. Nucleophilic Aromatic Substitution of Hydrogen; Academic Press: San Diego, 1994.
16. (c) Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. R. J. Am. Chem. Soc. 2001, 123, 12147.
17. (d) Cosimelli, B.; Lamartina, L.; Spinelli, D. Tetrahedron 2001, 57, 8903.
18. (e) Morely, J. O.; Mattewas, T. P. Org. Biomol. Chem. 2006, 4, 359.
19. (f) D'Anna, F.; Frenna, V.; Noto, R.; Pace, V.; Spinelli, D. J. Org. Chem. 2006, 71, 5144.
20. (a) Blanchard, S.; Rodriguez, I.; Kuehm-Caubère, C.; Renard, P.; Pfeiffer, B.; Guillaumet, G.; Caubère, P. Tetrahedron 2002, 58, 3513.
21. (b) Blanchard, S.; Rodriguez, I.; Caubère, P.; Guillaumet, G. Synlett 2002, 1356.
22. (c) Grig-Alexa, I. C.; Finaru, A. L.; Ivan, L.; Caubère, P.; Guillaumet, G. Tetrahedron Lett. 2004, 45, 2343.
23. (d) Grig-Alexa, I. C.; Garnier, E.; Finaru, A. L.; Ivan, L.; Jarry, C.; Léger, J.-M.; Caubère, P.; Guillaumet, G. Synlett 2004, 2000.
24. (e) Grig-Alexa, I. C.; Finaru, A. L.; Ivan, L.; Caubère, P.; Guillaumet, G. Synthesis 2006, 619.
25. (f) Grig-Alexa, I. C.; Finaru, A. L.; Caubère, P.; Guillaumet, G. Org. Lett. 2006, 8, 4187.
26. (a) Caubère, P.; Guillaumet, G.; Rodriguez, I.; Vinter-Pasquier, K.; Kuehm-Caubère, C.; Blanchard, S.; Atassi, G.; Pierre, A.; Pfeiffer, B.; Renard, P. P. Eur. Pat. Appl. EP 96986, 1999; Chem. Abstr. 2000, 132, 22978.
27. (b) Blanchard, S.; Rodriguez, I.; Tardy, C.; Baldeyrou, B.; Bailly, C.; Colson, P.; Houssier, C.; Léonce, S.; Kraus-Berthier, L.; Pfeiffer, B.; Renard, P.; Pierre, A.; Caubère, P.; Guillaumet, G. J. Med. Chem. 2004, 47, 978.
28. Makosza, M.; Wojciechowski, K. Heterocycles 2001, 54, 445.
29. Makosza, M.; Surowiec, M. Tetrahedron 2003, 59, 6261.
30. Makosza, M.; Stalinski, K. Synthesis 1998, 1631.
31. Makosza, M.; Sypniewski, M. Tetrahedron 1994, 50, 4913.
32. Makosza, M.; Paszewski, M. Synthesis 2002, 2203.
33. Stern, M. K.; Hileman, F. D.; Bashkin, J. K. J. Am. Chem. Soc. 1992, 114, 9237.
34. Stern, M. K.; Cheng, B. K. J. Org. Chem. 1993, 58, 6883.
35. (a) Stern, M. K.; Bashkin, J. K. U.S. Pat. 5117063, 1992; Chem. Abstr. 1992, 117, 89948.
36. (b) Bunnet, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273.
37. (c) Stahly, G. B. J. Org. Chem. 1985, 50, 3091.
38. (d) Davis, R. B.; Pizzini, L. C.; Benigni, J. D. J. Am. Chem. Soc. 1960, 82, 2913.
39. (e) Davis, R. B.; Pizzini, L. C. J. Org. Chem. 1960, 25, 1884.
40. (f) Treston, A.; Blakeley, R. L.; Zerner, B. J. Chem. Soc., Chem. Commun. 1980, 394.
41. (g) Makosza, M.; Staliński, K. Tetrahedron 1998, 54, 8797.
42. Bouisssane, L.; El Kazzouli, S.; Léger, J.-M.; Jarry, C.; Rakib, E. M.; Khouili, M.; Guillaumet, G. Tetrahedron 2005, 61, 8218.
43. Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.
44. Garnier, E.; Audoux, J.; Pasquinet, E.; Suzenet, F.; Poullain, D.; Lebret, B.; Guillaumet, G. J. Org. Chem. 2004, 69, 7809.
45. Turner, J. A. J. Org. Chem. 1983, 48, 3401.
46. Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435.
47. Krishnamurthy, S. Tetrahedron Lett. 1982, 23, 3315.
48. Zakrzewski, P.; Gowan, M.; Trimble, L. A.; Lau, C. K. Synthesis 1999, 1893.