Reactions of N-hydroxysuccinimide esters of anthranilic acids with anions of beta-keto esters. A new route to 4-oxo-3-quinolinecarboxylic acid derivatives.
A new approach for the synthesis of 4-oxo-3-quinolinecarboxylic acid derivatives is described. This methodology involves the C-acylation of the anions of appropriate beta-keto esters with novel N-hydroxysuccinimide esters of anthranilic acids. The intermediate C-acylation products 3 are spontaneously cyclized to afford 3-ethoxycarbonyl-4-oxoquinoline derivatives 4. The introduction of a variety of substituents at positions 1 and 2 of the quinoline ring is feasible with the selection of suitable anthranilic acids and beta-keto esters. The structure of the obtained 2-substituted 3-ethoxycarbonyl-4-oxoquinolines was confirmed by IR and NMR spectral data.
Mitsos
C
C
Chemical Engineering Department, National Technical University of Athens, Greece.
Zografos
A
A
Igglessi-Markopoulou
O
O
D002264:Carboxylic Acids / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015363:Quinolones / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013388:Succinimides / Q000737:chemistry; D062367:ortho-Aminobenzoates / Q000737:chemistry*
D002264:Carboxylic Acids; D004952:Esters; D007659:Ketones; D015363:Quinolones; D013388:Succinimides; D062367:ortho-Aminobenzoates