ビタミンB_1とホスゲンの反応

概要

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Depending upon reaction temperatures, the reaction of thiamine with phosgene in alkaline solution gave rise to two different compounds as follows. At 0-5℃, N-[1-(2-oxo-1,3-oxathian-4-ylidene) ethyl]-N-[(4-amino-2-methyl-5-pyrimidinyl) methyl]formamide (V) and at -20℃, bis-2-[N-(4-amino-2-methyl-5-pyrimidinylmethyl) formamido)-1-(2-hydroxyethyl) propenethiol carbonate (XVI). The structure of XVI could be established by the fact that the same compound was formed in the reaction of phosgene with O-tetrahydropyranylthiamine-Na followed by hydrolysis with hydrochloric acid. The structure of V was confirmed by UV, IR and NMR spectroscopies and by the observations that the treatment of V with NaOR, NaSR and amines produced O-carbalkoxythiamine, O-carbthioalkylthiamine and O-carbamoylthiamine, respectively. Similarly, hydroxyethylthiamine gave N-[1-(2-oxo-1,3-oxathian-4-ylidene) ethyl]-N-[(4-amino-2-methyl-5-pyrimidinyl) methyl]lactamide (VII) in the same way. Thermal decomposition of V was investigated. These new compounds showed thiamine-activity, and V is particularly remarkable among them, since it was quite readily absorbable from the intestine.
日本ビタミン学会の論文
1966-07-25