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

Content Provider	Royal Society of Chemistry (RSC)
Author	Tanwar, Babita Qadri, Mohammad Mohsin Singh, Madhulika Kumar, Dinesh Kumar, Asim Chakraborti, Asit K. Ansari, Imam Vaja, Maulikkumar D.
Copyright Year	2015
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.
Starting Page	9824
Ending Page	9833
Page Count	10
File Format	HTM / HTML PDF
ISSN	11440546
Volume Number	39
Issue Number	12
Journal	New Journal of Chemistry
DOI	10.1039/c5nj02010g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Ethyl acetoacetate Lewis Carbonyl group Aryl Methylene group
Content Type	Text
Resource Type	Article
Subject	Chemistry Materials Chemistry Catalysis

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