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Ethyl 1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylates by a tandem addition‐elimination‐S N Ar reaction
Author(s) -
Bunce Richard A.,
Lee Eric J.,
Grant Matthew T.
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.626
Subject(s) - chemistry , yield (engineering) , tandem , dimethylformamide , derivative (finance) , acetal , ring (chemistry) , medicinal chemistry , primary (astronomy) , reaction conditions , elimination reaction , cascade reaction , organic chemistry , combinatorial chemistry , catalysis , materials science , solvent , economics , financial economics , metallurgy , composite material , physics , astronomy
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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