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Fischer synthesis of indoles from 2,6-disubstituted arylhydrazones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A review of the literature data on the Fischer synthesis of indoles from 2,6-disubstituted arylhydrazones is given. As a result of their own experimental studies of the indolization of hydrazones from 8-R-N-amino-1,2,3,4-tetrahydroquinolines the authors established that no less than five different transformations of the cyclohexadienoneimine intermediate, including 1,2 and 1,4 shifts and splitting out of the substituent, may follow attack on the 8 position of the tetrahydroquinoline ring. Attack in the 10 position of the tetrahydroquinoline ring leads to another cyclohexadienoneimine, which undergoes indolization with the loss of apropylamine chain via a different mechanism. It was proved by experiments with labeled compounds that 1,3 migration of the methyl group (R=CH3) is the result of a double 1,2 shift, while the 1,4 shift is a direct reaction.

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Authors and Affiliations

  1. Institute of Industrial Chemistry, Center for the Study of Methods for the Synthesis and Stereochemistry of Special Organic Systems, Milan, Italy

    R. Fusco & F. Sannicoló

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  1. R. Fusco
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  2. F. Sannicoló
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 200–216, February, 1978.

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Fusco, R., Sannicoló, F. Fischer synthesis of indoles from 2,6-disubstituted arylhydrazones. Chem Heterocycl Compd 14, 157–172 (1978). https://doi.org/10.1007/BF00945329

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  • DOI: https://doi.org/10.1007/BF00945329

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