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Synthesis 2007(24): 3868-3876
DOI: 10.1055/s-2007-990896
DOI: 10.1055/s-2007-990896
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Nitro N,N′-Dipyridinylamines via Oxidative Nucleophilic Substitution of Hydrogen
Weitere Informationen
Received
18 April 2007
Publikationsdatum:
15. November 2007 (online)
Publikationsverlauf
Publikationsdatum:
15. November 2007 (online)
Abstract
The amination of 3-nitropyridines with aromatic amides generated from various aminopyridine derivatives proceeded unexpectedly in the position para to the nitro group, giving the oxidative nucleophilic substitution of hydrogen (ONSH) derived compounds. After optimization, this reaction allowed easy access to interesting 3-nitro-substituted N,N′-dipyridinylamines.
Key words
heterocycles - pyridines - amination - nucleophilic aromatic substitution - palladium
-
1a
O’Hagan D. Nat. Prod. Rep. 2000, 17: 435 -
1b
Pinder AR. Nat. Prod. Rep. 1992, 9: 491 -
1c
Plunkett AO. Nat. Prod. Rep. 1994, 11: 581 -
1d
Brody F.Ruby PR. Pyridine and Its Derivatives. Part 1. Synthetic and Natural Sources of the Pyridine Ring Interscience; New York: 1960. -
2a
Quintela JM.Peinador C.González L.Iglesias R.Paramá A.Alvarez F.Sanmartin ML.Riguera R. Eur. J. Med. Chem. 2003, 38: 265 -
2b
Van Rhee AM.Jiang J.Melman N.Olah ME.Stiles GL.Jacobson KA. J. Med. Chem. 1996, 39: 2980 -
2c
Bever CT. CNS Drug Rev. 1995, 1: 261 -
2d
Thomas G. Medicinal Chemistry Wiley-VCH; Weinheim: 2002. -
2e
Kleeman A.Engel J.Kutscher B.Reichert D. Pharmaceutical Substances 3rd ed.: Thieme; Stuttgart: 1999. - 3
Balboni G.Marastoni M.Merighi S.Borea PA.Tomatis R. Eur. J. Med. Chem. 2000, 35: 979 - 4
Chen B.-C.Hynes J.Pandit CR.Zhao R. Heterocycles 2001, 55: 951 - 5
Gfesser GA.Bayburt EK.Cowart M.DiDomenico S.Gomtsyan A.Lee C.-H.Stewart AO.Jarvis MF.Kowaluk EA.Bhagwat SS. Eur. J. Med. Chem. 2003, 38: 245 - 6
Brodbeck B.Püllmann B.Schmitt S.Nettekoven M. Tetrahedron Lett. 2003, 44: 1675 -
7a
Terrier F. Nucleophilic Aromatic Displacement Verlag Chemie; Weinheim: 1991. -
7b
Chupakhin ON.Chaushin VN.van der Plas HC. Nucleophilic Aromatic Substitution of Hydrogen Academic Press; San Diego: 1994. -
7c
Niles JC.Wishnok JS.Tannenbaum SR. J. Am. Chem. Soc. 2001, 123: 12147 -
7d
Cosimelli B.Lamartina L.Spinelli D. Tetrahedron 2001, 57: 8903 -
7e
Morely JO.Mattewas TP. Org. Biomol. Chem. 2006, 4: 359 -
7f
D’Anna F.Frenna V.Noto R.Pace V.Spinelli D. J. Org. Chem. 2006, 71: 5144 -
8a
Blanchard S.Rodriguez I.Kuehm-Caubère C.Renard P.Pfeiffer B.Guillaumet G.Caubère P. Tetrahedron 2002, 58: 3513 -
8b
Blanchard S.Rodriguez I.Caubère P.Guillaumet G. Synlett 2002, 1356 -
8c
Grig-Alexa IC.Finaru AL.Ivan L.Caubère P.Guillaumet G. Tetrahedron Lett. 2004, 45: 2343 -
8d
Grig-Alexa IC.Garnier E.Finaru AL.Ivan L.Jarry C.Léger J.-M.Caubère P.Guillaumet G. Synlett 2004, 2000 -
8e
Grig-Alexa IC.Finaru AL.Ivan L.Caubère P.Guillaumet G. Synthesis 2006, 619 -
8f
Grig-Alexa IC.Finaru AL.Caubère P.Guillaumet G. Org. Lett. 2006, 8: 4187 -
9a
Caubère P,Guillaumet G,Rodriguez I,Vinter-Pasquier K,Kuehm-Caubère C,Blanchard S,Atassi G,Pierre A,Pfeiffer B, andRenard PP. inventors; Eur. Pat. Appl. EP 96986. ; Chem. Abstr. 2000, 132, 22978 -
9b
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 - 10
Makosza M.Wojciechowski K. Heterocycles 2001, 54: 445 - 11
Makosza M.Surowiec M. Tetrahedron 2003, 59: 6261 - 12
Makosza M.Staliński K. Synthesis 1998, 1631 - 13
Makosza M.Sypniewski M. Tetrahedron 1994, 50: 4913 - 14
Makosza M.Paszewski M. Synthesis 2002, 2203 - 15
Stern MK.Hileman FD.Bashkin JK. J. Am. Chem. Soc. 1992, 114: 9237 - 16
Stern MK.Cheng BK. J. Org. Chem. 1993, 58: 6883 -
17a
Stern MK, andBashkin JK. inventors; U.S. Pat. 5117063. ; Chem. Abstr. 1992, 117, 89948 -
17b
Bunnet JF.Zahler RE. Chem. Rev. 1951, 49: 273 -
17c
Stahly GB. J. Org. Chem. 1985, 50: 3091 -
17d
Davis RB.Pizzini LC.Benigni JD. J. Am. Chem. Soc. 1960, 82: 2913 -
17e
Davis RB.Pizzini LC. J. Org. Chem. 1960, 25: 1884 -
17f
Treston A.Blakeley RL.Zerner B. J. Chem. Soc., Chem. Commun. 1980, 394 -
17g
Makosza M.Staliński K. Tetrahedron 1998, 54: 8797 - 18
Bouisssane L.El Kazzouli S.Léger J.-M.Jarry C.Rakib EM.Khouili M.Guillaumet G. Tetrahedron 2005, 61: 8218 - 19
Yin J.Buchwald SL. Org. Lett. 2000, 2: 1101 - 20
Garnier E.Audoux J.Pasquinet E.Suzenet F.Poullain D.Lebret B.Guillaumet G. J. Org. Chem. 2004, 69: 7809 - 21
Turner JA. J. Org. Chem. 1983, 48: 3401 - 22
Zhang Z.Mao J.Zhu D.Wu F.Chen H.Wan B. Tetrahedron 2006, 62: 4435 - 23
Krishnamurthy S. Tetrahedron Lett. 1982, 23: 3315 - 24
Zakrzewski P.Gowan M.Trimble LA.Lau CK. Synthesis 1999, 1893