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Communication | Regular issue | Vol 45, No. 11, 1997, pp.2109-2112
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7964
A Novel Abnormal Rearrangement in the Fischer Indole Synthesis

Hideaki Fujii, Akira Mizusuna, Ryuji Tanimura, and Hiroshi Nagase*

*Basic Research Laboratories, Toray Industries, Inc., 111, Tebiro, Kamakura, Kanagawa, 248, Japan

Abstract

In the Fischer indole synthesis of naltrexone N-methyl-N-(5,6,7,8-tetrahydro-1-naphthyl)hydrazone, an abnormal rearrangement of the fused 6-membered ring was observed. This abnormal rearrangement was not observed without the N-alkyl group of the hydrazone. The mechanism for the unexpected products was assumed to involve the [3,3] sigmatropic rearrangement at the substituted and more hindered ortho position and the subsequent rearrangement of the fused 6-membered ring via a spiro intermediate.