1. Ethyl 1,4-dihydro-4-oxo-3-quinolinecarboxylates by a tandem addition-elimination-SNAr reaction
- Author
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Matthew T. Grant, Richard A. Bunce, and Eric J. Lee
- Subjects
Dimethyl acetal ,chemistry.chemical_compound ,Addition elimination ,Primary (chemistry) ,chemistry ,Tandem ,Nucleophilic aromatic substitution ,Yield (chemistry) ,Organic Chemistry ,Organic chemistry ,Ring (chemistry) ,Derivative (chemistry) - 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-SNAr reaction. The synthesis of the starting material as well as procedural details and a mechanistic scenario are presented. J. Heterocyclic Chem., (2011).
- Published
- 2011
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