Syntheses of Medium-Sized Heterocycles Using an Intramolecular Michael Reaction
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概要
- 論文の詳細を見る
1,2,3,5-Tetrahydro-2-oxo-4,1-benzoxazepine-3-acetates (5,13,16), 2,3,5,6-tetrahydro-2-oxo-1H-4,1-benzoazocine-3-acetates (21), and 1,2,3,5,6,7-hexahydro-2-oxo-4,1-benzoxazonine-3-acetate (25) were obtained from 3-[[2-(ω-hydroxyalkyl)phenyl]carbamoyl]acrylates (4,12,15,20,24) by the intramolecular Michael addition previously developed for the synthesis of 3,4-dihydro-2H-1,4-benzoxazine-2-acetates. In the case of 5-phenyl-3-oxo-4,1-benzoxazepine-3-acetates (13), the 3,5-cis and 3,5-trans isomers were obtained in a ratio of 1 : 1. Under basic conditions, each isomer was equilibrated to a mixture of cis- and trans-13 in a ratio of 1 : 3. A deuterium exchange experiment revealed that the isomerization proceeded through the retro-Michael reaction. The stereochemistry of trans-13e was confirmed by X-ray analysis.Among the compounds (13) synthesized, N-isopropyl (cis-13c), N-benzyl (cis- and trans-13e) and N-phenethyl (cis-13f) derivatives showed considerable anxiolytic activity in the conflict test in rats.
- 公益社団法人日本薬学会の論文
- 1986-01-25
著者
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後藤 義一
Central Research Division, Takeda Chemical Industries, Ltd.
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野口 俊作
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
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後藤 義一
武田薬品工業(株)中央研究所
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舛岡 豊
武田薬品工業(株)中央研究所
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舛岡 豊
Central Research Division, Takeda Chemical Industries, Ltd.,
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故 朝子
Central Research Division, Takeda Chemical Industries, Ltd.,
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故 朝子
武田薬品工業(株)中央研究所
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