YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Vitamin B1及び諸関係化合物の研究 第27報
N-置換Thiothiazolone (2) 化合体及びVitamin B1同族体の生成に関する研究 その1
岩津 岳夫松川 泰三
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1952 年 72 巻 3 号 p. 354-358

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Condensation of 2-ethyl-4-amino-5-aminomethylpyrimidine (VI) with γ-aceto-γ-chloropropyl acetate (IV) or its alcohol (X), in the presence of carbon disulfide and ammonia, respectively yields α-aceto-γ-acetoxypropyl N-[2-ethyl-4-aminopyrimidyl (5)]-methyldithiocarbamate (VII) or α-aceto-γ-hydroxypropyl N-[2-ethyl-4-aminopyrimidyl (5)]-methyldithiocarbamate (XI). Both (VIII) and (XI) give 3-[2′-ethyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-hydroxyethylthiothiazolone (2) (VIII) by heating their respective solution in diluted hydrochloric acid. Heating their respcetive caustic alkali solution or heating their crystals to above their decomposition points results in the formation of 2-thio-7-ethyl-1, 2, 3, 4-tetrahydropyrimido-(4·5-d)-pyrimidine (IX). Oxidation of (VIII) with hydrogen peroxide in acid medium, followed by treatment with barium chloride gives, with a good yield, 3-[2′-ethyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-hydroxyethylthiazolium chloride hydrochloride (XVIII). Acetylation of (VIII) with acetic anhydride an pyridine yields 3-[2′-ethyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-acetoxyethylthiothiazolone (2). Use of 2-benzyl-4-amino-5-aminomethylpyrimidine (XII) in place of 2-ethyl-4-amino-5-aminomethylpyrimidine (VI) allows similar reactions to proceed.

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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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