Title:
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Fischer indole reaction in batch and flow employing a sulfonic acid resin: synthesis of pyrido[2,3-a]carbazoles
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Author:
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Bosch, Caroline; López-Lledó, Pablo; Bonjoch i Sesé, Josep; Bradshaw, Ben; Nieuwland, Pieter J.; Blanco-Ania, Daniel; Rutjes, Floris P. J. T.
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Other authors:
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Universitat de Barcelona |
Abstract:
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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. Keywords: Fischer indole synthesis, one-pot synthesis, continuous-flow synthesis, sulfonic acid resin, immobilized reagents, pyrido[2,3-a]carbazoles |
Subject(s):
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-Síntesi en fase sólida -Compostos heterocíclics -Àcids orgànics -Síntesi orgànica -Solid-phase synthesis -Heterocyclic compounds -Organic acids -Organic synthesis |
Rights:
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, 2016
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Document type:
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Article |
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