Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction

Rapid synthesis of quinoline-4-carboxylic acid derivatives has been achieved by reaction of 2-methoxy acrylates or acrylamides with N-arylbenzaldimines in acetonitrile under InCl3 catalysis and microwave irradiation. Isolated yields up to 57% within 3 min have been obtained. The Lewis acid and the m...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2005-10, Vol.3 (20), p.3794-3804
Main Authors: Duvelleroy, Dorothée, Perrio, Cécile, Parisel, Olivier, Lasne, Marie-Claire
Format: Article
Language:English
Subjects:
Acrylates - chemistry
Acrylates - radiation effects
Alkylation
Amides - chemistry
Amides - radiation effects
Computer Simulation
Imines - chemistry
Imines - radiation effects
Indium - chemistry
Microwaves
Molecular Structure
Quinolines - chemical synthesis
Quinolines - chemistry
Quinolines - radiation effects
Stereoisomerism
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Summary:Rapid synthesis of quinoline-4-carboxylic acid derivatives has been achieved by reaction of 2-methoxy acrylates or acrylamides with N-arylbenzaldimines in acetonitrile under InCl3 catalysis and microwave irradiation. Isolated yields up to 57% within 3 min have been obtained. The Lewis acid and the microwave activation appeared as crucial parameters for the reaction. The role of indium chloride and ytterbium triflate was specified using 13C NMR data and model theoretical studies.
ISSN:1477-0520
1477-0539
DOI:10.1039/b509400c