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

RA Bunce, EJ Lee, MT Grant

Index: Bunce, Richard A.; Lee, Eric J.; Grant, Matthew T. Journal of Heterocyclic Chemistry, 2011 , vol. 48, # 3 p. 620 - 625

Full Text: HTML

Citation Number: 9

Abstract

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- ...