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Issue 12, 2015
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Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines

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Abstract

The scope and limitations of metal salt Lewis acid catalysts were examined for the selectivity control for the formation of Friedländer and non-Friedländer products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)3 emerged as the most effective catalyst for the selective/exclusive formation of the Friedländer product. The generality of the In(OTf)3-catalysed Friedländer reaction was demonstrated by the reaction of differently substituted 2-aminoarylketones with various carbonyl compounds containing an active methylene group (e.g., β-ketoesters, cyclic/acyclic β-diketones, cyclic/acylic ketones, and aryl/heteroaryl methyl ketones) under solvent-free conditions affording the desired quinolines in 75–92% yields.

Graphical abstract: Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines

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Publication details

The article was received on 30 júl. 2015, accepted on 08 okt. 2015 and first published on 13 okt. 2015


Article type: Paper
DOI: 10.1039/C5NJ02010G
Author version available: Download Author version (PDF)
Citation: New J. Chem., 2015,39, 9824-9833
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    Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines

    B. Tanwar, D. Kumar, A. Kumar, Md. I. Ansari, M. M. Qadri, M. D. Vaja, M. Singh and A. K. Chakraborti, New J. Chem., 2015, 39, 9824
    DOI: 10.1039/C5NJ02010G

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