Voges-Proskauer反応の呈色機構に関する研究

概要

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The mechanism of the Voges -Proskauer reaction was investigated using 1-pheny-1,2-propanedione (I), morpholinoamidine (II) and α-naphthol in the presence of alkali (Barritt's method). From the nuclear magnetic resonance and mass spectral data, the structures of pigments obtained in the presence of α-naphthol (Barrit's method) were determined as 2-(2-morpholino-4-phenyl-1H-5-imidazolylmethylidene)-1,2-dihydro-1-oxo-naphthalene (Pigment A') and 2-morpholino-5-phenyl-4-(2-morpholino-4-phenyl-1H-5-imidazolylmethylidene)-isoimidazole (Pigment C'). Pigment C' was also obtained in the absence of α-naphthol (O'Meara's method). By the reaction of I and II in a nitrogen gas stream, 2-morpholino-4-hydroxy-4-methyl-5-phenyl-4-isoimidazole (Compound D') was obtained. Compound D' produced Pigment A' by the reaction with α-naphthol in an aerobic alkaline solution, and in the absence of α-naphthol, Compound D' produced Pigment C'. These results indicate that the Voges-Proskauer reaction proceeds through an intermediate such as Compound D'.
公益社団法人日本薬学会の論文
1973-07-25