Studies on Seven-membered Ring Compounds. X. Nitration of 5-Hydroxycyclohepta [b] pyrrol-6 (1H)-one Derivatives and their Rearrangement Reaction to Indole Derivatives.
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概要
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3-Aryl-5-hydroxycyclohepta [b] pyrrol-6 (1H)-one were synthesized by the similar manner as previously described. Nitration of 5-hydroxycyclohepta [b] pyrrol-6 (1H)-one derivatives (VII and Va) gave mononitro derivatives (VIIIa and VIIIb). The properties of the mononitro derivatives (VIIIa and VIIIb) were examined and it was discovered that VIIIa and VIIIb underwent rearrangement by aqueous alkali to 4-nitroindole derivatives (Xa and Xb). In order to determine the structure of the products being obtained by the rearrangement reaction, the cyclization of phenylpyruvic acid 4-carboxy-3-nitrophenylhydrazone (XIVa) was investigated. Moreover, the nitro groups of the products were proved to be in 4-potition by infrared spectra analysis and oxidative degradations. Therefore, above-mentioned mononitro derivatives were established to be 4-nitro-5-hydroxycylohepta [b] pyrrol-6 (1H)-one derivatives.
- 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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- Studies on Seven-membered Ring Compounds. X. Nitration of 5-Hydroxycyclohepta [b] pyrrol-6 (1H)-one Derivatives and their Rearrangement Reaction to Indole Derivatives.