Chemija / Chemistry
 ISSN 0235-7216 ISSN 2424-4538 (online) |
2012 m. Nr. 1 Reaction of dialkyl acetylenedicarboxylates with ninhydrin
in the presence of secondary amines: synthesis of alkyl 4-(benzyl(alkyl)amino)-1’,3’,5- trioxo-1’,3’- dihydro- H-spiro[furan-2,2’-indene]-3-carboxylate derivatives
A three-component domino reaction approach between a secondary amine, dialkyl acetylenedicarboxylate and ninhydrin that affords novel alkyl 4-(benzyl(alkyl)amino)-1’,3’,5- trioxo-1’,3’-dihydro-5H-spiro[furan-2,2’-indene]-3-carboxylate derivatives is reported. The reaction sequence consists of an initial Michael-addition of secondary amines to dialkyl acetylenedicarboxylates, followed by aldol-like reaction with ninhydrin, and then γ-lactonization to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.
Keywords: dialkyl acetylenedicarboxylates, ninhydrin, furan, Michael-addition, secondary amine |
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