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.
The three-component reaction of triphenylphosphine, dialkyl hex-2-en-4-ynedioate and arylidene-1,3-indanedione in dry DME at room temperature furnishes functionalized triphenylphosphanylidene-substituted 1′,3′-dihydrospiro[cyclopentane-1,2′-inden]-2-enes in 75–92% yields.
The three-component reaction of triphenylphosphine, dialkyl acetylenedicarboxylate, and 2-arylideneindane-1,3-dione in dry DME at 0 °C to room temperature resulted in functionalized 4-(triphenyl-λ 5-phosphanylidene)-1′,3′-dihydrospiro[cyclopentane-1,2′-inden]-2-enes in 65-87% yields. An unusual feature of the reaction is the retention of the triphenylphosphanylidene group in the spiro product.
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