Color Reaction Product of Urea with Diacetyl Monoxime and Glucuronolactone. II. On the Reaction of Butylurea with Diacetyl, 1-Phenyl-1,2-propanedione, 1-Phenyl-1-hydroxyimino-2-propanone, and 1-Phenyl-2-hydroxyimino-1-propanone

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The reaction products of the color reactions of butylurea and glucuronolactone with 1-phenyl-1,2-propanedione, two positional isomers of its monoxime and diacetyl in aqueous phosphoric acid were investigated. The results showed that all reactions, regardless of the difference in the color developing reagent employed, gave 2,2'-dioxo-4,5'-diimidazolylmethane (I) derivatives as main products, and that the reactions of diacetyl and its monoxime gave tetrahydroimidazo [4,5-d] imidazole-2,5-dione (II) derivatives as common products. All of these compounds developed visible colors in acidic media, and the colors received strong hyperchromic shifts by the duration of the keeping time at room temperature. Because every color had close relations with the colors of the respective reaction mixtures, I and II derivatives were indicated to have significant responsibilities for the colorations. In spite of the poor reproducibility of isolation, an isolation of 1,4-dimethyl-4-acetyl-3 (or 6)-butylcarbamoylimino-1,2-cyclohexen-6 (or 3)-one (III) from the reaction mixture of butylurea, diacetyl and glucuronolactone was also mentioned, because its responsibility for the color reaction was not excluded. The influence of glucuronolactone on the formation of the reaction products was shown to be negligible and glucuronolactone was assumed to play its role in the process of the stabilization of the color developed.
公益社団法人日本薬学会の論文
1971-01-25