The Fischer Indole Syntheis is the most important method of preparing substituted indoles.

Fischer Indole Synthesis Overview

One of the oldest reactions in organic chemistry, the Fischer Indole synthesis is the condensation of a substituted phenylhydrazine and a carbonyl compound under acidic conditions to produce an aromatic heterocycle indole.

 

Named Reactions in Organic Synthesis

Fischer Indole Synthesis Mechanism

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    Named Reactions eBook

    Named Reactions in Organic Synthesis eBook

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    History of the Fischer Indole Synthesis

    In 1883, E. Fischer and F. Jourdan treated pyruvic acid 1-methylphenylhydrazone with alcoholic hydrogen chloride and generated 1-methylindole-2-carboxylic acid. Preparing indoles by heating the arylhydrazones of either aldehydes or ketones in the presence of a protic or Lewis acid is now known as the Fischer indole synthesis. Since its discovery, it has remained the most important method of preparing substituted indoles.

    Main features of the Fischer indole synthesis:

    • The indole formation can be carried out as a one-pot synthesis, as it is not necessary to isolate the intermediate arylhydrazones
    • Unsymmetrical ketones give two region-isomeric 2,3-disubstituted indoles, with the region-selectivity dependent on acidity of the medium, substitution of the hydrazine, and steric effects
    • 1,2-diketones can give both mono and bis-indoles, the mono-indoles usually forming with strong acid catalysts in refluxing alcohols

    Other Heterocycle Formation Reactions

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