The DABCO promoted domino reaction of 1‐(2‐hydroxyphenyl)‐3‐phenylprop‐2‐en‐1‐ones and alkyl propiolate or dialkyl but‐2‐ynedioate in toluene at high temperature resulted in methyl 3‐(2‐hydroxybenzoyl)‐1‐naphthoates or dimethyl 3‐(2‐hydroxybenzoyl)naphthalene‐1,2‐dicarboxylate in moderate to good yields. The hydroxyl group played a crucial rule in the reaction. The reaction mechanism of this formal [4+2] cycloaddition reaction was believed with initially formation of methyl 3‐(2‐cinnamoylphenoxy)acrylate, intramolecular Diels‐Alder reaction, ring‐opening of benzo[b]xanthene and aromatization process.
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