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Fischer indole synthesis of 3-benzyl-1H-indole via conductive and dielectric heating

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Chemistry of Heterocyclic Compounds Aims and scope

As a part of designing one-pot synthesis conditions for a combination of Heck isomerization and Fischer indolization (HIFI sequence), a model reaction was studied using 3-phenylpropanal and phenylhydrazine to furnish 3-benzyl-1H-indole under conductive and dielectric heating. While Amberlyst® 15 as an acidic catalyst or T3P® (propylphosphonic acid cyclic anhydride) as a condensation agent gave high yields of 3-benzyl-1H-indole under both conductive and dielectric heating, these agents were not compatible with the conditions of the initial Heck isomerization. However, the catalyst-free thermal process for the indolization step proceeded with good yields in conjunction with the preceding Heck isomerization in a one-pot process under dielectric heating in N-methylpyrrolidone as a solvent.

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The authors cordially thank the Fonds der Chemischen Industrie for financial support.

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Authors and Affiliations

  1. Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225, Düsseldorf, Germany

    Jesco Panther, Julian Rechmann & Thomas J. J. Müller

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  1. Jesco Panther
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  2. Julian Rechmann
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  3. Thomas J. J. Müller
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Correspondence to Thomas J. J. Müller.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(11), 897–903

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Panther, J., Rechmann, J. & Müller, T.J.J. Fischer indole synthesis of 3-benzyl-1H-indole via conductive and dielectric heating. Chem Heterocycl Comp 52, 897–903 (2016). https://doi.org/10.1007/s10593-017-1983-2

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