Fischer indolization of ethyl pyruvate 2-bis(2-methoxyphenyl)hydrazone and new insight into the mechanism of Fischer indolization. (Fischer indolization and its related compounds. XXVII)

DOI: 10.1248/cpb.43.1287

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1287 - 1293 (1995)

Update date:2022-07-31

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Authors:

Murakami

Watanabe

Otsuka Otsuka

Iwata Iwata

Yamada Yamada

Yokoyama

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Article abstract of DOI:10.1248/cpb.43.1287

In connection with studies on the direction of cyclization in the Fischer indolization of substituted diphenylhydrazones, the Fischer indolization of ethyl pyruvate 2-bis(2-methoxyphenyl)hydrazone (6) was carried out. The result showed that cyclization in Fischer indolization of diphenylhydrazone does not always proceed to the electron-richer nucleus, but depends on the conformation of the enehydrazine. Thus, the Fischer indolization should proceed via a [3,3] sigmatropic route, with an electronic effect.

Full text of DOI:10.1248/cpb.43.1287

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