Voges-Proskauer 発色反応の機構に関する研究

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The mechanism of the Voges-Proskauer reaction was investigated using 1-phenyl-1, 2-propanedione (I), morpholinoamidine (II), α-naphthol in the presence of alkali (Barritts method) and uisng (I), (II) in the presence of alkali (OMearas method). The pigments obtained by Barritts method and OMearas method were isolated as crystals by column chromatography. From the data of NMR and mass spectra, the structures of pigments obtained by Barritts and OMearas method were determined as 2-(2-morpholino-4-phenyl-1H-5-imidazolylmethylidene) 1, 2-dihydro-1-oxonaphthalene (VI) and 2-morpholino-5-phenyl-4-(2-morpholino-4-phenyl-1H-5- imidazolylmethylidene) isoimidazol(VII), respectively. Structures of 2-(2-morpholino-4-methyl-1H-5-imidazolylmethylidene)-1, 2-dihydro-1-oxonaphthalene (III) and 2-morpholino-5-methyl-4-(2-morpholino-4-methyl-1H-5-imidazolylmethylidene)-isoimidazol (IV) were determined previously by NMR, mass and IR spectroscopy. On the other hand, 2-morpholino-4-hydroxy-4-methyl -5-phenyl-4-isoimidazol (V) was obtained as a solid, from the reaction mixture of (I) and (II) in N2. (VI) and (VII) were also derived by the reaction with (V) and α-naphthol-sodium hydroxide solution and the reaction with (V) and sodium hydroxide solution in air, respectively. These results indicate the Voges-Proskauer reaction proceeds through (V), which is followed by the production of (VI) and (VII).
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