Quinizarin boroacetate and 1,4-diaminoanthraquinone diboroacetate as dienophiles

Abstract
Quinizarin boroacetate undergoes a Diels-Alder reaction with cyclopentadiene to give (after hydrolysis) a mixture of exo- and endo-leuco isomers (III) in the ratio 1 : 2·6 which can be oxidised to a bridged 2,3-cycloquinizarin derivative (IV; XOH); cycloaddition with acyclic dienes is accompanied by aromatisation.

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