Vitamin B₁関係化合物の研究 (第16報)

S-Acylthiamine誘導体について

抄録

Acylation of thiamine with alkali gave O, S-diacylthiamine (IV) (IVa: R=p-NO₂C₆H₄-, IVb: R=C₆H₅-, IVc: R=CH₃-). S-Acylthiamine hydrochloride (V) (Va: R=p-NO₂C₆H₄-, Vb: R=C₆H₅-) was formed by allowing a solution of (IV) in 25% ethanolic hydrochloric acid to stand. This S-acylthiamine (V) underwent S→O rearrangement in acid or alkaline medium to give O-acylthiamine (VII) (VIIa: R=p-NO₂C₆H₄-, VIIb: R=C₆H₅-). From the fact that S-acylthiamine easily undergoes rearrangement to O-acylthiamine, the formation of O, S-diacylthiamine from thiamine can be explained.