Abstract
In order to synthesize 10-amino-2, 3, 6-trimethoxy-10, 11-dihydrodibenzo[b, f]oxepine, the phenylhydrazone (V) of the ketone compound (II) was submitted to catalytic reduction in the presence of palladium-carbon catalyst and an indole derivative (VI) was obtained unexpectedly. To clarify this mechanism, desoxybenzoin phenylhydrazone (VIII) was submitted to the same reduction and an indole derivative (IX) was also obtained. IX is also obtained from VIII by Fischer's indole synthesis, as there was no depression of the melting point on their admixture. The reason why the indole derivative (VI) is not obtained from V by the usual method of Fischer's indole synthesis seems to be due to the lability of the phenylhydrazone (V), which is easily oxidized and resinifies, and the derivative is formed only in a reductive medium.
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