Studies on Seven-membered Ring Compounds. XI. Bromination of 5-Hydroxycyclohepta [b] pyrrol-6 (1H)-one Derivatives and Synthesis of 3-(2-Aminoethyl)-2-carboxy-5-hydroxycyclohepta [b] pyrrol-6 (1H)-one.
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概要
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Bromination of 5-hydroxycyclohepta [b] pyrrol-6 (1H) -one was examined. Namely, bromination of 2-ethoxycarbonyl-5-hydroxy-3-phenylcyclohepta [b] pyrrol-6 (1H)-one (Ib) afforded only 4-bromo-2-ethoxycarbonyl-5-hydroxy-3-phenylcyclohepta [b] pyrrol-6 (1H)-one (IIb), and 5-hydroxy-3-phenylcyclohepta [b] pyrrol-6 (1H) -one (VI) afforded 2-bromo (VII), and 2,4-dibromo-5-hydroxy-3-phenylcyclohepta [b] pyrrol-6 (1H)-one (VIII). Hydrolysis of IIb with alkali afforded 4-bromo-2-carboxy-5-hydroxy-3-phenylcyclohepta [b] pyrrol-6 (1H)-one (III) without rearrangement reaction. Reaction of III with aqueous ammonia afforded 2-carboxy-4,5-dihydroxy-3-phenylcyclohepta [b] pyrrol-6 (1H)-one (V). A sevenmembered ring compound having a similar structure to serotonin, 3- (2-aminoethyl) -2-carboxy-5-hydroxycyclohepta [b] pyrrol-6 (1H)-one hydrochloride (XII) was prepared.
- 公益社団法人日本薬学会の論文
- 1963-11-25
著者
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佐藤 裕信
Central Research Laboratories Sankyo Co. Ltd.
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佐藤 裕信
Takamine Research Laboratory, Sankyo Co., Ltd.
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