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Tandem Reaction of 4‐Halo‐1,3‐Dicarbonyl Compounds with Alkynes towards 4‐Vinyl‐3(2H)‐Furanones and 3(2H)‐Furanone fused 2‐Pyridones

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Synthesis of 4-vinyl-3(2H)-furanones from 4-halo-1,3-dicarbonyl compounds with alkynes was achieved via a tandem Michael addition and intramolecular cyclization pathway. In addition, a regioisomer formation of the same product via a stepwise [2+2] cycloaddition, sequential 4π-ring opening, and an intramolecular cyclization has also been noted. Formation of 3(2H)-furanone fused 2-pyridone from the reaction of 4-bromo-3-oxo-N-alkyl (aryl) butanamide with activated alkynes was also realised.


Abstract

A facile synthetic route of 4-vinyl-3(2H)-furanones from the reaction of 4-halo-1,3-dicarbonyl compounds and alkynes is reported, a reaction taking place via tandem Michael addition and intramolecular cyclization. The formation of a side-product (regioisomer) by a stepwise [2+2] cycloaddition between enolate (of the 4-halo-1,3-dicarbonyl compound) and activated alkyne followed by a sequential 4π-ring opening and an intramolecular cyclization has also been noted. Another interesting observation was the formation of 3(2H)-furanone fused 2-pyridone from the reaction of 4-bromo-3-oxo-N-alkyl(aryl)butanamide with activated alkynes. All reactions were found to be general affording the corresponding substituted/fused 3(2H)-furanones in satisfactory to good yields.

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