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Dinitrofuran is readily available from 2-nitrofuran by treatment with concentrated nitric acid. The reaction of this compound with various nucleophilic reagents proceeds by an addition/elimination sequence (SNAr) to furnish substituted 5-nitrofurans in good yield. Diels— Alder cycloaddition of the resulting activated furans with various π-systems affords transient (4+2)-cycloadducts that undergo nitro group elimination and subsequent aromatization to produce polysubstituted phenols.

A novel synthesis of polysubstituted phenols using the SNAr reaction of 2,5-dinitrofuran