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Herein,we disclosed a molecular iodine-mediated formal [2+1+1+1] cycloaddition reaction for the construction of pyrrolo[2,1-a]isoquinolines.This new reaction involves intermolecular cycloaddition of two in situ-generated azomethine ylides with α,β-unsaturated ketone intermediates from acetophenones and 1,2,3,4-tetrahydroisoquinolines using DMSO as a source of methylene.