Synthesis of polyhalogenated 2-(phenylamino)pyridines by thermal amination reactions

Synthesis

Volumn , Issue 10, 2009, Pages 1651-1654

  Waldvogel, Siegfried R ^a   Faust, Andreas ^b   Barkmann, Werner ^c   Fröhlich, Roland ^c   Wolff, Oliver ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY HOSPITAL MÜNSTER   (Germany)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Aminations; Anilines; Nucleophilic aromatic substitutions; Polyhalogenated; Pyridines; Tetramethylpiperidine

Indexed keywords

AMINATION REACTION; AMINATIONS; HIGH MOLECULAR WEIGHT; NUCLEOPHILIC AROMATIC SUBSTITUTIONS; POLYHALOGENATED; SOLVENT FREE; TETRAMETHYLPIPERIDINE; THERMAL CONVERSION;

AMINES; ANILINE; AROMATIC COMPOUNDS; PALLADIUM; PYRIDINE;

AMINATION;

2,2,6,6 TETRAMETHYLPIPERIDINE DERIVATIVE; 2,6 DIBROMOPYRIDINE; HALIDE; PALLADIUM; PIPERIDINE DERIVATIVE; POLYHALOGENATED 2 (PHENYLAMINO)PYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; MOLECULAR WEIGHT; SYNTHESIS;

EID: 67650082403     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216642     Document Type: Article

References (30)

1. (a) Klebl, B.; Baumann, M.; Hoppe, E.; Brehmer, D.; Daub, H.; Keri, G.; Varga, Z.; Marosfalvi, J.; Oerfi, L. WO 2006,021,458, 2006.
2. (b) Chung, J. Y. L.; Cvetovich, R. J. Curr. Opin. Drug Discovery Dev. 2006, 9, 792.
3. (a) Babu, P. A.; Narasu, M. L.; Srinivas, K. ARKIVOC 2007, (ii), 247.
4. (b) De Clercq, E.; Naesens, L. J. Clin. Virology 2006, 37, S82.
5. (c) Gassel, M.; Breitenlechner, C.; Herrero, S.; Engh, R.; Bossemeyer, D. Inhibitors of Protein Kinases and Protein Phosphates, In Handbook of Experimental Pharmacology, Vol. 167; Pinna, L. A.; Cohen, P. T. W., Eds.; Springer: Heidelberg, 2005, 85.
6. (a) Recent review: Breit, B. Angew. Chem. Int. Ed. 2005, 44, 6816.
7. (b) Waloch, C.; Wieland, J.; Keller, M.; Breit, B. Angew. Chem. Int. Ed. 2007, 46, 3037.
8. (c) Breit, B.; Seiche, W. Angew. Chem. Int. Ed. 2005, 44, 1640.
9. Dalton King, H.; Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Epperson, J. R.; Higgins, M. A.; Kung, J. E.; Marcin, L. R.; Sloan, C. P.; Mattson, G. K.; Molski, T. F.; Krause, R. G.; Bertekap, R. L.; Lodge, N. J.; Mattson, R. J.; Macor, J. E. Bioorg. Med. Chem. Lett. 2007, 17, 5647.
10. Scholz, U.; Schlummer, B. In Science of Synthesis, Vol. 31; Ramsden, C., Ed.; Georg Thieme Verlag: Stuttgart, 2007, Chap. 28, 1565.
11. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
12. (b) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
13. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
14. (a) Kaila, N.; Green, N.; Li, H.; Hu, Y.; Janz, K.; Gavrin, L. K.; Thomason, J.; Tam, S.; Powell, D.; Cuozzo, J.; Hall, J. P.; Telliez, J.; Hsu, S.; Nickerson-Nutter, C.; Wang, Q.; Lin, L. Bioorg. Med. Chem. 2007, 15, 6425.
15. (b) Stoit, A. R.; den Hartog, A. P.; Mons, H.; van Schaik, S.; Barkhuijsen, N.; Stroomer, C.; Coolen, H. K. A. C.; Reinders, J. H.; Adolfs, T. J. P.; van der Neut, M.; Keizer, H.; Kruse, C. G. Bioorg. Med. Chem. Lett. 2008, 18, 188.
16. (c) Matsumoto, K.; Minatogawa, H.; Toda, M.; Munakata, M. Heterocycles 1990, 31, 1217.
17. (d) Laufer, S. A.; Hauser, D. R. J.; Liedtke, A. J. Synthesis 2008, 253.
18. (a) Schröter, S.; Bach, T. Heterocycles 2007, 74, 569.
19. (b) Guthmann, H.; Könemann, M.; Bach, T. Eur. J. Org. Chem. 2007, 632.
20. (c) Delgado, O.; Heckmann, G.; Müller, H. M.; Bach, T. J. Org. Chem. 2006, 71, 4599.
21. (d) Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
22. (a) Delgado, O.; Müller, H. M.; Bach, T. Chem. Eur. J. 2008, 14, 2322.
23. (b) Müller, H. M.; Delgado, O.; Bach, T. Angew. Chem. Int. Ed. 2007, 46, 4771.
24. Faust, A.; Wolff, O.; Waldvogel, S. R. Synthesis 2009, 155.
25. Kampmann, D.; Stuhlmüller, G.; Simon, R.; Cottet, F.; Leroux, F.; Schlosser, M. Synthesis 2005, 1028.
26. Wagav, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240.
27. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
28. Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr., Sect. A 2003, 59, 228.
29. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467.
30. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.