Studies on Pyrimidine Derivatives and Related Compounds. XCIV. On the Oxidation Products of 2-Substituted-2,3-dihydro-4H-1,4-thiazin-3-one Derivatives. (2)
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概要
- 論文の詳細を見る
Hydrogen peroxide oxidation of 4-(4-amino-2-methylpyrimidin-5-yl) methyl-6-(2-hydroxyethyl)-2-(2-methoxyphenyl)-4-methyl-2,3-dihydro-4H-1,4-thiazin-3-one (1c) gave N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[1-(2-oxido-1,2-oxathiolan-3-yliden)ethyl] (2-methoxyphenyl)oxalamide (3b) and 2-oxido-1,2-oxathiolane-3-spiro-3'-[1'-(4-amino-2-methylpyrimidin-5-yl)methyl-4'-hydroxy-2'-methylene-4'-(2-methoxyphenyl)-tetrahydropyrrol-5'-one] (6). The former product (3b) was transformed into another product (6) under oxidative reaction conditions and 6 led to the known 1-(4-amino-2-methylpyrimidin-5-yl)methyl-4-hydroxy-3-(2-hydroxyethyl)-4-(2-methoxyphenyl)-2-methyl-Δ^2-pyrrolin-5-one (4) and 2-aza-2-(4-amino-2-methylpyrimidin-5-yl)methyl-4-hydroxy-4-(2-methoxyphenyl)-1-methyl-8-oxabicyclo [3.3.0] octan-3-one (5) on acid or alkali treatment. On the other hand, an oxalamide (3d) having a 2-anisyl substituent was recovered under the same reaction conditions. The same reaction with 2-aryl-4-benzyl-2,3-dihydro-4H-1,4-benzothiazin-3-ones (12a-c) afforded 2-aryl-4-benzyl-2-hydroxy-2,3-dihydro-4H-1,4-benzothiazin-3-ones (13a-c), bis-(2-aryloxalylaminophenyl)-1,1'-disulfide (14a-b) and 2-aryl-4-benzyl-3-oxo-2,3-dihydro-4H-1,4-benzothiazine-1,1-dioxide (15a-c), while 4-benzyl-2-methyl-2,3-dihydro-4H-1,4-benzothiazine-1,3-dioxide (16b) was mainly obtained in the oxidation of the 2-methyl derivative (12d), which was converted into 4-benzyl-2-hydroxy-2-methyl-2,3-dihydro-4H-1,4-benzothiazin-3-oxide (13d) via a Pummerer-type rearrangement. The reaction mechanism is discussed.
- 公益社団法人日本薬学会の論文
- 1980-03-25
著者
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高見沢 映
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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原田 紘
Shionogi Research Laboratories, Shionogi & Co., Ltd.,
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高見沢 映
Shionogi Research Laboratory Shionogi And Co. Ltd.
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高見沢 映
Shionogi Research Laboratory Shionogi & Co. Ltd.
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原田 紘
Shionogi Research Laboratory Shionogi And Co. Ltd.
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原田 紘
Shionogi Research Laboratories Shionogi & Co. Ltd.
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