Abnormal Fischer Indolization and Its Related Compounds. XXII. : Fischer Indolization of Ethyl Pyruvate 2-(2-Chloro- and 2,6-Dichlorophynyl)methylhydrazones
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概要
- 論文の詳細を見る
The Fischer indolization of ethyl pyruvate 2-(2-chlorophenyl)methylhydrazone (17) with HCl/EtOH proceeded rapidly to give six 1-methylindoles, ethyl 7-chloro (19), 6-chloro (22), and unsubstituted (24)-1-methylindole-2-car-boxylates, and dichloro derivatives (21,23,and 26), whereas no indolization had occurred with the correspinding NH-hydrazone, as described in a previous paper. This result shows that the abnormal Fischer indolization of 2-chloro-phenylhydrazones with HCl/EtOH occurred in an ortho-C_6 fashion, in the same manner as that of the corresponding 2-methoxyphenylhydrazones (1 and 2).The Fischer indolization of ethyl pyruvate 2-(2,6-dichlorophenyl)methylhydrazone (18) with HCl/EtOH did not occur at all, whereas the reaction with ZnCl_2/AcOH gave a low yield of ethyl 5,7-dichloro-3-methylindole-2-carboxylate (36), which was formed by migration of the N-methyl group during Fischer indolization.
- 公益社団法人日本薬学会の論文
- 1990-03-25
著者
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石井 永
Faculty of Pharmaceutical Sciences, Chiba University
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石川 勉
Faculty of Pharmaceutical Sciences, Chiba University
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石川 勉
千葉大薬
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石川 勉
千葉大院薬
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石井 永
Faculty Of Pharmaceutical Sciences Chiba University
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村上 泰興
School of Pharmaceutical Sciences, Toho University
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村上 泰興
東邦大・薬
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村上 泰興
School Of Pharmaceutical Science Toho University
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