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SELECTIVE SYNTHESIS OF 2-METHYLIDENEPYRROL-3-ONES FROM DIYNONES AND AMINES

Alena S. Pankova, Nadezhda D. Cherepanova, Pavel Golubev, Mikhail A. Kuznetsov
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Abstract


Addition of primary amines to 1-phenyl-5-trimethylsilylpenta-1,4-diyn-3-one with subsequent cyclization affords 5-phenyl-2-(trimethylsilylmethylidene)-1,2-dihydro-3H-pyrrol-3-ones. Both electron-rich and electron-deficient anilines and alkyl amines provide regio- and stereoselective formation of single product in high yields. The two-step transformation benefits from full atom economy, operational simplicity, and no need for additives and catalysts.

Keywords


alkynes; diynones; enamines; pyrrolones; cyclization

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