The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives

Authors : Javad SAFAEIGHOMI, Fariba SALIMI, Ali RAMAZANI

Pages : 485-492

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Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :A 3-component domino reaction approach between a primary amine, a dialkyl acetylenedicarboxylate, and 2-oxo-2- phenylacetaldehyde that affords novel alkyl 2-benzoyl-4-alkylamino- 5-oxo-2,5-dihydro-3-furan carboxylate derivatives is reported. The reaction sequence consists of an initial Michael addition of primary amines to dialkyl acetylenedicarboxylates, followed by an aldol-like reaction with 2-oxo-2-phenylacetaldehyde, and then g -lactonization to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.
Keywords : Dialkyl acetylenedicarboxylates, 2 oxo 2 phenylacetaldehyde, primary amines, furan, Michael addition