Chemical and Pharmaceutical Bulletin p. 1910 - 1919 (1993)
Update date:2022-09-26
Topics:
Murakami
Watanabe
Yokoyama
Naomachi
Iwase
Watanabe
Morihata
Okuyama
Kamakura
Takahashi
Atoda
Tojo
Morita
Ishii
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, phenylhydrazones 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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Doi:10.1248/cpb.58.160
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