SYNTHESIS OF REGIOISOMERIC 6,9-(CHLOROFLUORO)-SUBSTITUTED BENZO[G]QUINOLINE-5,10-DIONES, BENZO[G]ISOQUINOLINE-5,10-DIONES AND 6-CHLORO-9-FLUOROBENZO[G]QUINOXALINE-5,10-DIONE

Treatment of difluoro or chloro fluoro-substituted benzyl bromides 5a- c with zinc dust in tetrahydrofuran leads to the corresponding benzyli c zinc bromides 6a-c. These organometallics on treatment with chlorosu bstituted heterocyclic esters 4A and 4B mediated by nickel catalysis u ndergo couplings to yield dihalobenzyl substituted heterocyclic esters 7Aa-c and 7Ba-c. Treatment of 4c with 6c under Pd catalysis leads to 7Cc. The acids 8, prepared by hydrolysis of these esters, with treatme nt of fuming sulfuric acid undergo cyclizations and oxidations to yiel d the desired regioisomeric dihalo-substituted heterocyclic quinones 2 .