Reaction of Tetracyanoethylated Cyclohexanones with Water in Acidic Medium

摘要

It was reported earlier that 4-oxoalkane-1,1,2,2-tetracarbonitriles depending on different factors react with hydrohalic acids to form 2-halopyridine-3,4-dicarbonitriles [1-3], 2-halo-6-hydroxy-5,6-dihydroxy-pyridine-3,4,4(1H)-tricarbonitriles [4], pyrrolo[3,4-c] pyrrole-1,3,4,6(2H,3aH,5H,6aH)-tetraones [1], 3-halo-6-oxo-2,7-diazabicyclo[3.2.1]oct-3-ene-4,5-dicarbo-. nitriles [5]. At the same time the influence of the structure of 4-oxoalkane-1,1,2,2-tetracarbonitriles on the reaction with aqueous sulfuric acid was not studied. Only reaction of 50% sulfuric acid with 3-methyl-4-oxopentane-1,1,2,2-tetracarbonitrile to afford 5,6-di-methyl-2-oxo-1,2-dihydropyridine-3,4-dicarbonitrile in 10% yield has been reported [3].