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A new method was developed for the facile one-pot multicomponent construction of heterocycle-fused spiro compounds containing chromanone and pyrrolidinyl spirooxindoles, two potential pharmacophores, in one molecule through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction of carboxylic acid group-activated chromones 1 with isatin-derivated azomethine ylides based on molecular hybridization strategy. A wide variety of products with three contiguous stereocenters including a spiro quaternary stereocenter were smoothly prepared with high efficiency (up to 87% yield and 20:1 diastereomeric ratio). This method could offer libraries of architecturally diverse and multiple pharmacore collections, potentially useful in medicinal chemistry. [ABSTRACT FROM AUTHOR]