Reaktion #365157

Reaktionsgleichung

quinolone

quinolone

4-bromo-3-fluoro-benzoyl chloride

malonic acid monoethyl ester monopotassium salt

→

benzoyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigemay be formed

Vorschrift

As an alternative to the quinolone synthesis outlined above, the quinolone nucleus may be formed using the route illustrated in Scheme II. Similar methodology for the preparation of quinolones was first described in German patent application DE3142854. Starting from a 4-bromo-3-fluoro-benzoyl chloride, condensation with malonic acid monoethyl ester monopotassium salt gives a benzoyl acetate that is subsequently reacted with triethyl orthoformate. The resulting ethoxymethylene derivative is reacted with a primary amine and cyclized to the quinolone.

Quelle