α-Diketone類によるGuanidine類の反応(第3報)9,10-Phenanthraquinoneと1-ナフトールによるグアニジンの発色反応生成物の構造

概要

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The structure of a pigment I produced from guanidine with 9,10-phenanthraquinone and 1-naphthol in the presence of alkali was investigated. Pigment I was found to be a ternary product formed by the condensation of one equivalent each of guanidine, 9,10-phenanthraquinone, and 1-naphthol. The molecular formula and IR spectrum of I were identical with those of pigment II isolated from the reaction with 4-chloro-1-naphthol instead of 1-naphthol. Pigment I could be derived from 2-amino-1H-phenanthro [9,10-d] imidazole (V) which was obtained as a fluorescent product in the reaction of guanidine or mono-substituted guanidines with 9,10-phenanthraquinone. Therefore, the structure of pigment I was concluded to be N-(1'H-phenanthro-[9,10-d] imidazolyl)-1,4-naphthoquinone monoimine. Thin-layer chromatography also proved that pigment I was formed in the reaction mixture of 9,10-phenanthraquinone, 1-naphthol, and mono-substituted guanidines, regardless of the kinds of guanidines. Based on these results, the mechanism of this color reaction was discussed.
社団法人日本薬学会の論文
1979-03-25