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

Tanwar, Babita ; Kumar, Dinesh ; Kumar, Asim ; Ansari, Md. Imam ; Qadri, Mohammad Mohsin ; Vaja, Maulikkumar D. ; Singh, Madhulika ; Chakraborti, Asit K. (2015) Friedlander annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines New Journal of Chemistry, 39 (12). pp. 9824-9833. ISSN 1144-0546

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2015...

Related URL: http://dx.doi.org/10.1039/C5NJ02010G

Abstract

The scope and limitations of metal salt Lewis acid catalysts were examined for the selectivity control for the formation of Friedlander and non-Friedlander 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 Friedlander 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.

Item Type:Article
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ID Code:100244
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