Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Fischer Indolization of Variously ortho-Substituted Phenylhydrazones (Fischer Indolization and Its Related Compounds. XXV)
Yasuoki MURAKAMI, Toshiko WATANABE, Yuusaku YOKOYAMA, Junko NAOMACHI, Haruo IWASE, Noriko WATANABE, Michiyo MORIHATA, Naomi OKUYAMA, Hiroyuki KAMAKURA, Tomoko TAKAHASHI, Hideko ATODA, Toshiaki TOJO, Kenji MORITA, Hisashi ISHII
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Keywords: Fischer indolization, indole, phenylhydrazone, ortho-substituted, migration, substituent effect
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1993 Volume 41 Issue 11 Pages 1910-1919

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Abstract

Various kinds of ethyl pyruvate 2-(2-substituted phenyl)hydrazones (1) were subjected to Fischer indolization with acid catalysts. All the phenylhydrazones gave corresponding normal 7-substituted indoles (2). In addition, phenyl-hydrazones whose ortho-substituent is electron-donative or has a central atom with an unshared electron pair tended to give the 4- or 5-substituted indole (3), which was produced by migration of the ortho-substituent during cyclization, whereas those whose ortho-substituent is electron-attractive tended to give little or no such abnormal product. The kind of acid catalyst used had some effect on the yield ratio of products but not on the kind of products.

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