Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction

A method for the synthesis of both symmetric and asymmetric fused spiro[4.4]-nonane-dione derivatives has been developed. It is based on a Diels–Alder reaction of spiro[4.4]nona-2,7-diene-1,6-dione as a dienophile component followed by immediate aromatization of the adduct. An active diene component can be generated using the tetrabromoxylene/NaI system, the 1,3-diphenylisobenzofuran/BF 3 system, or substituted cyclones.