Action of Cyanogen Bromide on Thiamine. IV. Studies on 2-Methyl-6-(1-methyl-2-thiocyanato-4-hydroxy-1-butenyl)-5,6-dihydropyrimido[4,5-d]pyrimidine (Neocyanothiamine).

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2-Methyl-6-(1-methyl-2-thiocyanato-4-hydroxy-1-butenyl)-5,6-dihydropyrimido[4,5-d]-pyrimidine(V) is decomposed into thiamine (III), N-(1-methyl-2-thiocyanato-4-hydroxy-1-butenyl)-N-[(2-methyl-4-amino-5-pyrimidinyl)methyl]formamide (IV), thiamine anhydride (VI), thiochrome (VIII), and HCNO by the action of water. The yield decreases in the order of (III), (IV), (VI), and (VIII), while in hot water, the yield of (VIII) is increased. The action of hydrous acid on (V) gives (IV). On the other hand, the reaction of (V) with acid under anhydrous condition gives its salt (XV), which is converted into 2-imino-3-(2-methyl-4-formamido-5-pyrimidinyl)methyl-3a-methyl-3a, 5,6,6a-tetrahydrofuro[2,3-d]-thiazole (XIII) by the action of sodium hydrogencarbonate and water. (XIII) changes to 2-imino-3-(2-methyl-4-amino-5-pyrimidinyl)methyl-3a-methyl-3a, 5,6,6a-tetrahydrofuro[2,3-d]thiazole (XII) with a loss of formic acid by the action of mineral and acetic acid or sodium hydroxide. When heated with water, (XIII) also changes to 2,8a-dimethyl-5a, 6,7,8a-tetrahydrofuro-[2,3-h]thiochromine (VII) through (XII) produced by hydrolysis liberating ammonia.
公益社団法人日本薬学会の論文
1960-04-25