| Abstract: | A general method for preparing 2-substituted-4-oxo-3-quinolinecarboxylic acids and 2-substituted-4-oxo-1,8-naphthyridine-3-carboxylic acids as new analogs in the quinolone class of antiinfectives has been developed. The reaction of a Grignard reagent in the presence of copper(I) iodide with the 4-oxo-3-quinolinecar-boxylic acid esters and 4-oxo-1,8-naphthyridine-3-carboxylic acid esters yields the desired 2-substituent. Re-introduction of the 2,3-double bond is effected by phenylselenation of the 3-position, oxidation to the selen-oxide, and in situ syn-elimisation. Depending on the degree of steric crowding between the 2-substituent and the 3-carboxylic acid group, hydrolysis of the ester to the carboxylic acid could be carried out under acidic or basic conditions. |
