- Turkish Journal of Chemistry
- Vol: 36 Issue: 3
- The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of p...
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 Safaei-ghomi, Fariba Salimi, Ali Ramazani
Pages : 485-492
View : 13 | Download : 4
Publication Date : 9999-12-31
Article Type : Makaleler
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