Reaction of dialkyl acetylenedicarboxylates with nin-hydrin in the presence of secondary amines: Synthesis of alkyl 4-(benzyl(alkyl)amino)-1',3',5-trioxo- 1',3'- dihydro-5H-spiro[furan-2,2'-indene]-3-carboxylate derivatives

چکیده مقاله

A three-component domino reaction approach between a secondary amine, dialkyl acety-lenedicarboxylate and ninhydrin that afords novel alkyl 4-(benzyl(alkyl)amino)-1',3',5-trioxo-1',3'-dihydro-5H-spiro[furan-2,2'-indene] -3-carboxylate derivatives is reported. Te 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 aford the products. Tis cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules. © 2012 Lietuvos mokslu̧ akademija.