A new synthetic route to 7‐halo‐1‐cyclopropyl‐6‐fluoro‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acid, an intermediate for the synthesis of quinolone antibacterial agents

doi:10.1002/JHET.5570240134

Paper

A new synthetic route to 7‐halo‐1‐cyclopropyl‐6‐fluoro‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acid, an intermediate for the synthesis of quinolone antibacterial agents

Published 1987 · H. Egawa, M. Kataoka, Shibamori Koh-Ichiro

Journal of Heterocyclic Chemistry

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17

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0

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Abstract

Starting from m-fluorotoluene, 7-chloro-6-fluoro- and 6,7-difluoro-1-cyclopropyl-1,4-dihydro-4-oxoquino-line-3-carboxylic acids, 3 and 16 were synthesized. Compounds 3 and 16 are useful intermediates for the synthesis of a class of quinolone antibacterial agents. The synthetic route involves two processes; i) construction of the quinoline ring by an intramolecular cyclization accompanied by the elimination of a nitro group and ii) introduction of fluorine atom by replacement of a nitro group with potassium fluoride. 7-(3-Amino-1-pyrroli-dinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (18) was prepared from 3 or 16. The antibacterial activity of 18 compares favorably with that of ciprofloxacin (2).

Study Snapshot

This study presents a new synthetic route to 7-halo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, an intermediate for the synthesis of quinolone antibacterial agents, with promising antibacterial activity compared

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

A new synthetic route to 7‐halo‐1‐cyclopropyl‐6‐fluoro‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acid, an intermediate for the synthesis of quinolone antibacterial agents

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References

Pyridonecarboxylic acids as antibacterial agents. 4. Synthesis and antibacterial activity of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4 -dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid and its analogues.

Three compounds, 1-ethyl-, 1-vinyl-7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (33

In vitro activity of Bay 09867, a new quinoline derivative, compared with those of other antimicrobial agents

Bay 09867 shows high in vitro activity against gram-negative bacteria, particularly against gentamicin-resistant strains, and is more active than other agents tested.

ENHANCED EFFECT OF SPRAY-DRIED POTASSIUM FLUORIDE ON FLUORINATION

Spray-dried potassium fluoride is a more effective fluorinating agent than calcine-dried potassium fluoride, making it a promising alternative for organic compounds containing activated halogen atoms.

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