84655-70-9Relevant articles and documents
Syntheses with Nitriles. 62. 3,5-Dicyanopyridine Derivatives by Vilsmeier Formylation of Malononitrile and Tetracyanopropenides (2)
Mittelbach, Martin,Junek, Hans
, p. 1021 - 1024 (2007/10/02)
Reaction of malononitrile with dimethylformamide and phosphorus oxychloride gave (dimethylaminomethylene)malononitrile (1), 4-chloro-7-methyl-5,7-diaza-1,3,5-octatriene-1,1,3-tricarbonitrile (3a) and the pyridine 2.Compounds 3a and 3b as well as the triaza-derivative 3c may also be obtained by treatment of tetracyanopropenides 4a-c with dimethylformamide and phosphorus oxychloride.Ring closures were achieved by heating 3 under alkaline or acidic conditions.Substitution of chlorine in 3a with aromatic amines provided 1-aryl-1,2-dihydro-2-imino-3,5-pyridinedicarbonitriles 7.Hydrolysis of 7 gave the 2-oxo-derivatives 8.