Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Fischer Indolization and Its Related Compounds. VI. Effect of Reagents and Substituent of the ortho-Substituted Phenylhydrazone on Abnormal Fischer Indolization
石井 永村上 泰興古瀬 徳夫細谷 勝弘池田 仁三郎
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1973 年 21 巻 7 号 p. 1495-1505

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Treatment of ethyl pyruvate 2-methoxyphenylhydrazone (1) with Lewis acid gave 5-substituted and/or 5-methoxy-indole products with ethyl 7-methoxyindole-2-carboxylate (2) as a main product. It contrasts strikingly with the results reported in the previous paper1) on a reaction center of the abnormal Fischer indolization. It was also found that differences of the acid strength of the reagent and of the electron density on a benzene ring due to introduction of some other additional substituents could be the determinant for the direction of the adnormal transformation.

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