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Synthesis 1991; 1991(10): 835-838
DOI: 10.1055/s-1991-26585
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Synthesen mit Nitrilen, LXXXVIII1; Cyan-Nitropropenide - Synthone zur Herstellung von Nitropyridinen

Gerhard H. Reidlinger* , Hans Junek
  • *Institut für Organische Chemie, Abteilung für Angewandte Organische Chemie, Karl-Franzens-Universität Graz, Heinrichstraße 28, A-8010 Graz, Austria
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Publication Date:
29 April 2002 (online)

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Syntheses with Nitriles, LXXXVIII;1 Cyanonitropropenides - Synthons for the Preparation of Nitropyridines Nitroacetonitrile reacts with triethyl orthoformate, orthoacetate and orthopropionate, respectively in presence of pyridine to the pyridinium salts of 1,3-dicyano-1,3-dinitro-2-propen-1-ides. With ethoxymethylenemalononitrile nitroacetonitrile yields 1,1,3-tricyano-3-nitropropenide, which can be cyclized with sodium methoxide or ethoxide to 2-alkoxy-6-amino-3-cyano-5-nitropyridines. Ether cleavage of the latter leads to 6-amino-3-cyano-5-nitro-2(1H)-pyridone, subsequent chlorination gives the corresponding 2-chloropyridine, suitable for nucleophilic substitutions. By hydrolysis of the nitrile group 6-amino-5-nitro-3-pyridinecarboxylic acid derivatives are obtained.