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)

J. Bálint, G. Egri, E. Fogassy, Zsolt Böcskei, Kálmán Simon, Antal Gajáry, Antal Friesz

Research output: Article

37 Citations (Scopus)

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 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.

Original languageEnglish
Pages (from-to)1079-1087
Number of pages9
JournalTetrahedron Asymmetry
Volume10
Issue number6
DOIs
Publication statusPublished - márc. 26 1999

Fingerprint

flumequine
Quinolizines
Bactericides
Sulfonic Acids
Enantiomers
sulfonic acid
enantiomers
Carboxylic Acids
Carboxylic acids
carboxylic acids
Salts
Nuclear magnetic resonance
X-Rays
Anti-Bacterial Agents
salts
X rays
nuclear magnetic resonance
Acids
synthesis
configurations

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

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). / Bálint, J.; Egri, G.; Fogassy, E.; Böcskei, Zsolt; Simon, Kálmán; Gajáry, Antal; Friesz, Antal.

In: Tetrahedron Asymmetry, Vol. 10, No. 6, 26.03.1999, p. 1079-1087.

Research output: Article

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AU - Bálint, J.

AU - Egri, G.

AU - Fogassy, E.

AU - Böcskei, Zsolt

AU - Simon, Kálmán

AU - Gajáry, Antal

AU - Friesz, Antal

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