Tetramethylmesoxalamide and Tetramethyl-1,3-Dithiomesoxalamide

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Abstract
The chemistry of mesoxalic acid derivatives was investigated many years ago.2 For example, Curtiss demonstrated that dimethyl mesoxalate added ethanol to produce a stable isolatable hemiketal,3 whereas the corresponding diethyl ester presumably gave the ethyl hemiketal at −15°, but it could not be isolated.4 These esters are readily hydrated, and strongly dehydrating conditions are required to regain the ketone.5 Guyot and Esteva6 condensed mesoxalic esters with aromatic compounds in sulfuric acid to produce the corresponding α-hydroxyarylmalonates and diaryl-malonates. Curtiss3,4 showed that aromatic amines condensed with ethyl mesoxalate to produce carbonyl adducts (Schiffs bases, hydroxyamines), while Heinisch7 showed that aliphatic amines produced 2-hydroxy-2-alkylamino-N,N′-dialkylmalonamides. Other derivatives, such as mesoxalonitrile,8 and several different amides7,9 have been reported. Brudnoy10 reported an unusual imidazole on treatment of diethyl mesoxalate with ammonia, although earlier reports7,9 showed that the hydrate, 2,2-dihydroxymalonamide, was obtained in good yield in this reaction.

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