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Ethyl 1,4-dihydro-4-oxo-3-quinolinecarboxylates by a tandem addition-elimination-SNAr reaction

✍ Scribed by Richard A. Bunce; Eric J. Lee; Matthew T. Grant

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
196 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The ethyl 1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylate ring structure, important in several drug compounds, has been prepared in two steps from ethyl 2‐(2‐fluorobenzoyl)acetate. Treatment of this β‐ketoester with N,N‐dimethylformamide dimethyl acetal gives a 97% yield of the 2‐dimethylaminomethylene derivative. Reaction of this β‐enaminone with primary amines in N,N‐dimethylformamide at 140°C for 48 h then affords the 1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylate esters in 60–74% yields by a tandem addition‐elimination‐S~N~Ar reaction. The synthesis of the starting material as well as procedural details and a mechanistic scenario are presented. J. Heterocyclic Chem., (2011).

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