4-Iminobarbiturates

Tautomerism of 4-iminobarbiturates depends upon the presence of a substituent on the N(3)atom. The ultraviolet, infrared, proton nuclear magnetic resonance, 13C-nuclear magnetic resonance and mass spectrum data show that 3-alkylated compounds present an imido system while 3-unalkylated ones are char...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 36; no. 2; p. 563
Main Authors GIRAUD, CHRISTOPHE, GUEUTIN, CLAIRE, LAFONT, OLIVIER, GUERNET, MICHEL, MIOCQUE, MARCEL
Format Journal Article
LanguageEnglish
Published Tokyo Japan Science and Technology Agency 01.02.1988
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Summary:Tautomerism of 4-iminobarbiturates depends upon the presence of a substituent on the N(3)atom. The ultraviolet, infrared, proton nuclear magnetic resonance, 13C-nuclear magnetic resonance and mass spectrum data show that 3-alkylated compounds present an imido system while 3-unalkylated ones are characterized by an amidinoketone system.The electrochemical bahavior of these two groups was studied by polarography, cyclic voltammetry and controlled potential electrolysis in dipolar aprotic solvents (dimethyl sulfoxide and hexamethyl phosphoric triamide), and was found to be related to the structure : the reduction of 3-substituted compounds is more difficult (about 0.2 V) than the reduction of 3-unalkylated products. The monoelectronic mechanism of this reduction was determied and confirmed by the electrochemically induced formation of an anion which can be alkylated using methyl iodide.
ISSN:0009-2363
1347-5223