Studies on Pyrimidine Derivatives and Their Related Compounds. XCI. On the Oxidation Products of 2-Substituted-1,4-thiazin-3-one Derivatives
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概要
- 論文の詳細を見る
On treatment of 2-p-chlorophenylthiazinothiamine (Ib) with hydrogen peroxide, 2-hydroxy-2-p-chlorophenylthiazinothiamine (IIb) was obtained. Similar reaction products of phenyl-and methylthiazinothiamine (Ia and Ie) were reinvestigated and found to be IIb analogues (IIa and IIe, respectively). Reactions of IIa, IIb or IIe with acetic anhydride afforded the corresponding N-(2-methyl-4-aminopyrimidin-5-yl) methyl-N-(2-acetylthio-4-amino-1-methyl-1-butenyl) aryl (or methyl) oxalamide (IIIa, IIIb or IIIe, respectively). Treatment of 2-o-tolylthiazinothiamine (Ic) with hydrogen peroxide gave N-[1-(2-oxido-1,2-oxathiolan-3-ylidene) ethyl]-N-[(2-methyl-4-aminopyrimidin-5-yl) methyl]-o-tolyloxalamide (VIIIc) as a major product and similar treatment of o-methoxyphenylthiazinothiamine (Id) with hydrogen peroxide gave 1-(2-methyl-4-aminopyrimidin-5-yl) methyl-2-methyl-3-(2-hydroxyethyl)-4-hydroxy-4-(2-methoxyphenyl)-⊿^2-pyrrolin-5-one (XV). Oxidations of Ia, Ic and Id with m-chloroperbenzoic acid also gave VIIIc and the corresponding VIIIc analogues (VIIIa and VIIId, respectively). The mechanisms of these reactions are discussed as shown in Chart 2.
- 公益社団法人日本薬学会の論文
- 1978-03-25
著者
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高見沢 映
新潟薬科大学
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牧野 逸男
塩野義製薬株式会社研究所
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牧野 逸男
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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牧野 逸男
塩野義製薬研究所
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高見沢 映
Shionogi Research Laboratory Shionogi & Co. Ltd.
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原田 絋
Shionogi Research Laboratory, Shionogi and Co., Ltd.
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原田 絋
Shionogi Research Laboratory Shionogi And Co. Ltd.
関連論文
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