Synthesis, absolute configuration and intermediates of 9-fluoro- 6,7- dihydro-5-methyl-1-oxo-1H,5H-benzo[i.j]quinolizine-2-carboxylic acid (flumequine)
The antibacterial agent 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H- benzo[i.j]quinolizine-2-carboxylic acid (flumequine) was synthesized in optically active form from 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ). Racemic FTHQ was resolved with the enantiomers of 3-bromocamphor-8- sulfonic acid. The configurations were established by X-ray structures of the two diastereoisomeric salts. Enantiomeric excesses were determined by 1H NMR analysis.
Balint, Jozsef,Egri, Gabriella,Fogassy, Elemer,Boecskei, Zsolt,Simon, Kalman,Gajary, Antal,Friesz, Antal