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)

Authors
Balint, J Egri, G Fogassy, E Bocskei, Z Simon, K Gajary, A Friesz, A
Citation
J. Balint et al., 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), TETRAHEDR-A, 10(6), 1999, pp. 1079-1087
Citations number
7
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
6
Year of publication
1999
Pages
1079 - 1087
Database
ISI
SICI code
0957-4166(19990326)10:6<1079:SACAIO>2.0.ZU;2-T
Abstract
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 a ctive form from 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ). Racem ic FTHQ was resolved with the enantiomers of 3-bromocamphor-8-sulfonic acid . The configurations were established by X-ray structures of the two diaste reoisomeric salts. Enantiomeric excesses were determined by H-1 NMR analysi s. (C) 1999 Elsevier Science Ltd. All rights reserved.