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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

✍ Scribed by A. Paul Krapcho; Cynthia E. Gallagher; Abdelhakim Hammach; Michael Ellis; Ernesto Menta; Ambrogio Oliva

Publisher: Journal of Heterocyclic Chemistry
Year: 1997
Tongue: English
Weight: 465 KB
Volume: 34
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570340105

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✦ Synopsis

Abstract

Treatment of difluoro or chloro fluoro‐substituted benzyl bromides 5a‐c with zinc dust in tetrahydro‐furan leads to the corresponding benzylic zinc bromides 6a‐c. These organometallics on treatment with chlorosubstituted heterocyclic esters 4A and 4B mediated by nickel catalysis undergo 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 treatment of fuming sulfuric acid undergo cyclizations and oxidations to yield the desired regioisomeric dihalo‐substituted heterocyclic quinones 2.

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