A General, Regiospecific Synthesis of Highly Substituted Quinones

Article abstract of DOI:10.1021/jo00365a043

A general route to a wide variety of substituted quinones (furyl, indolo, pyrrolo, quinolino, naphtho, and anthra) has been developed via the thermolysis (160 deg C, xylene) and subsequent oxidation (air or Ce⁴⁺) of 4-hydroxy-4-substituted-cyclobutenones (eq. 1) and 2-hydroxy-2-substituted-benzocyclobutenones which were formed by the regioselective addition of an appropriate aryl or heteroaryl (etc.) lithium reagent to the correspnding cyclobutenedione.