84655-67-4Relevant articles and documents
Competing transformations of 2-cyanoacetanilides in reactions with derivatives of ethoxymethylenemalonic acid
Tkachova, Valeriya P.,Gorobets, Nikolay Yu.,Tkachov, Roman P.,Musatov, Vladimir I.,Dyachenko, Vladimir D.
experimental part, p. 398 - 411 (2012/09/08)
Ethoxymethylenemalonodinitrile 1B and ethyl ethoxymethylenecyanoacetate 1C in cyclocondensations with 2-cyanoacetanilides 2 behave as a three-carbon fragment transfer reagent to afford the corresponding 5-cyano-and 5-ethoxycarbonyl-6-amino-1-aryl-3-cyanopyridin-2(1H)-one derivatives 7B and 8C. One carbon transfer described earlier for such reactions with a use of diethyl 2-(ethoxymethylene)malonate 1A was observed only as a side process in the case of 1C leading to 2-amino-5-cyano-6-oxo-N,1-diaryl-1,6-dihydropyridine-3- carboxamides. ARKAT-USA, Inc.
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.