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A synthetic approach to furyl- and benzofuryl-containing building blocks utilizing easily accessible substrates is reported. Cascade acid-catalyzed reactions of 2-methylfuran with α,β-unsaturated carbonyl compounds or salicyl alcohols followed by oxidation afford functionalized furans and benzofurans, respectively. Synthetic potential of the obtained products was demonstrated by synthesizing hetaryl-substituted heterocycles, which may find an application in materials chemistry.