Fischer Indole Reaction in Batch and Flow Employing a Sulfonic Acid Resin: Synthesis of Pyrido[2,3-a]carbazoles | Zendy

Caroline Bosch | Zendy; Pablo López-Lledó | Zendy; Josep Bonjoch | Zendy; Ben Bradshaw | Zendy; Pieter J. Nieuwland | Zendy; Daniel BlancoAnia | Zendy; Floris P. J. T. Rutjes | Zendy

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Fischer Indole Reaction in Batch and Flow Employing a Sulfonic Acid Resin: Synthesis of Pyrido[2,3-a]carbazoles

Author(s) -

Caroline Bosch,

Pablo López-Lledó,

Josep Bonjoch,

Ben Bradshaw,

Pieter J. Nieuwland,

Daniel BlancoAnia,

Floris P. J. T. Rutjes

Publication year - 2016

Publication title -

journal of flow chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.916

H-Index - 25

eISSN - 2063-0212

pISSN - 2062-249X

DOI - 10.1556/1846.2016.00016

Subject(s) - chemistry , amberlite , isomerization , phenylhydrazine , indole test , flow chemistry , sulfonic acid , organic chemistry , green chemistry , batch reactor , continuous flow , catalysis , medicinal chemistry , reaction mechanism , adsorption , physics , mechanics

An Amberlite IR 120 H-promoted one-pot Fischer indolization from a cis-decahydroquinoline using a range of phenylhydrazines led to compounds with the pyrido[2,3-a]carbazole scaffold. The process may be conducted either in batch mode or in a continuous manner in a flow reactor. The stereochemical course of the Fischer indole reaction changed in going from using free phenylhydrazine to the corresponding hydrochloride in batch conditions, whereas, with the short reaction times in continuous flow, no changes due to isomerization processes were observed.

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