Fischer Indole Synthesis

doi:10.1002/9781118695692.ch2

Indole Ring Synthesis 2016

DOI: 10.1002/9781118695692.ch2

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Fischer Indole Synthesis

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Cited by 3 publications

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“…Among the numerous methods for accessing indoles, the Fischer indole synthesis (FIS) introduced by Fischer in 1883 , continues to be commonly employed, with applications spanning small-scale drug discovery programs to large-scale manufacturing processes. , In a typical FIS, an aryl hydrazine is condensed with a carbonyl species (ketone or aldehyde) to provide the corresponding hydrazone that cyclizes in the presence of a Brønsted or Lewis acid at, generally, high temperatures (Scheme B).…”

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confidence: 99%

A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides

et al. 2022

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Indoles are among the most important N-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl diazoniums that sequentially activate the alkyl iodides through halogen-atom transfer and then serve as radical acceptors. The process operates under mild conditions and enables the preparation of densely functionalized indoles.

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A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides

et al. 2022

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Heumann Indole Flow Chemistry Process

et al. 2019

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Continuous flow chemistry has improved efficiency in the Heumann indole process. 3-Substituted indoles were prepared by three flow steps performed in succession in better overall yield and shorter reaction times relative to their batch counterparts. Novel 3-alkyl and 3-methoxyindoles were synthesized from their corresponding amino ketone and ester precursors by flow sequences featuring base-free alkylation with methyl bromoacetate in DMF, saponification, and cyclization with acetic anhydride and Et 3 N.

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A general approach to construct selenopheno[3,2-b]indole-cored molecules using Fischer indolization

Irgashev,

Steparuk

2024

Org. Biomol. Chem.

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A wide series of various selenopheno[3,2-b]indole-based compounds, including 2-aryl-substituted selenopheno[3,2-b]indoles as well as derivatives of benzo[4,5]selenopheno[3,2-b]indole, pyrido[3',2':4,5]selenopheno[3,2-b]indole, pyrazino[2',3':4,5]selenopheno[3,2-b]indole and chromeno[3',4':4,5]selenopheno[3,2-b]indol-6-one were prepared from the appropriate 3-aminoselenophen-2-carboxylates according one-pot two-step procedure...

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Fischer Indole Synthesis

Cited by 3 publications

References 391 publications

A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides

A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides

Heumann Indole Flow Chemistry Process

A general approach to construct selenopheno[3,2-b]indole-cored molecules using Fischer indolization

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