Reaction of Guanidines with α-Diketones. V. Mechanism of the Fluorescence Reaction of Monosubstituted Guanidines with 9,10-Phenanthraquinone

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Mechanism of the fluorescence reaction of monosubstituted guanidines with 9,10-phenanthraquinone was investigated. Benzylguanidine reacted with 9,10-phenanthraquinone in an alkaline solution to give 2-benzylideneamino-1H-phenanthro [9,10-d]-imidazole (II) as an intermediate of the fluorescence reaction. II easily underwent hydrolysis with HCl to give a fluorescent product, 2-amino-1H-phenanthro [9,10-d] imidazole hydrochloride monohydrate (I), and benzaldehyde. II also underwent partial hydrolysis in an alkaline solution to give the free base of I, and the free base reacted with 1-naphthol and 9,10-phenanthraquinone to give an indophenol pigment, N-(1H-phenanthro [9,10-d]-imidazolyl)-1,4-naphthoquinone monoimine (IV). Amidines also reacted with 9,10-phenanthraquinone in the presence of alkali to afford 2'-(substituted) spiro[9H-fluorene-9,4'-[4H] imidazol]-5'(3'H)/5'(1'H)-ones (VI and VII) which underwent an intramolecular rearrangement, as a non-fluorescent product.
公益社団法人日本薬学会の論文
1978-02-25