Nucleophilic Phosphine-Promoted Domino Reaction of Dialkyl Acetylenedicarboxylates and 3-Arylamino-1-methyl-1H-pyrrole-2,5-diones

Abstract

The three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH₂Cl₂ at room temperature resulted in functionalized 3-(triphenyl-λ⁵-phosphanylidene)succinates in nearly quantitative yields. However, tri(n-butyl)phosphine promoted reaction of dialkyl acetylenedicarboxylates and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH₂Cl₂ afforded functionalized pyrrolo[3,4-b]pyridine-4-carboxylates in satisfactory yields.

Key words

phosphine - electron-deficient alkyne - pyrrolo[3,4-b]pyridine - β-enamino amides - multicomponent reaction

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