Vitamin B1および諸関係化合物の研究 第97報
N-(1-Methyl-2-thiocyano-4-hydroxy-1-butenyl)-N-〔(2-methyl-4-amino-5-pyrimidinyl) methyl〕formamide (Cyanothiamine) およびその誘導体の研究 その5
1959 年 79 巻 2 号 p. 143-150
詳細
1959 年 79 巻 2 号 p. 143-150
N-(1-Methyl-2-thiocyano-4-hydroxy-1-butenyl)-N-[(2-methyl-4-amino-5-pyrimidinyl)-methyl] formamide (cyanothiamine) (I) is converted to N-[1-(2-thiacyclobutyliden)-ethyl]-N-[(2-methyl-4-amino-5-pyrimidinyl) methyl] formamide (II) on application of alkali to its aqueous solution. The presence of methanol in this reaction solvent results in concurrent formation of N-(1-methyl-2-methylthio-4-hydroxy-1-butenyl)-N-[(2-methyl-4-amino-5-pyrimidinyl) methyl] formamide (VII). These are all new specific reactions for 3-hydroxypropyl thiocyanate derivatives and is thought to go through intermediate products (XXI) and (XXII). Application of cyanogen bromide to 3-(2-methyl-4-amino-5-pyrimidinyl) methyl)-4-methyl-5-(1-hydroxyethyl) thiazolium salt (XIII) in alkaline state was found to result in direct formation of thiacyclopropylidene derivative (XXXVII) and thiocyano derivative (XLIII) was not isolated, as in the case of thiamine.
