Abstract: This paper reports an acid-catalyzed tandem cyclization reaction for one-pot efficiently synthesize multi-aromatic ring-fused3.3.1dioxazonane compounds. This method used 2-hydroxychalcone compounds and 2-naphtholas as raw materials to synthesize polycyclic O-heterocyclic compounds. The reaction mechanism is different from the tandem process caused by the traditional Michael addition. It is a process in which 2-hydroxychalcone is dehydrated by acid to form anthocyanin intermediates, and then electrophilic substitution/intramolecular addition cyclization with 2-naphthol to form polycyclic fused oxygen-heterocyclic compounds. The reaction atom economy is high, and the post-processing is simple. This method can obtain molecular diversity multi-aromatic ring-fused3.3.1dioxazonane compounds with a yield of 75%−92%, all of which were characterized and identified by ¹H NMR, ¹³C NMR, HRMS and IR.