Abstract
Increasing interests have been invested in the development of synthetic strategies toward the construction of spiro[pyrrolidine-2,3′-oxindole], which is the core structural skeleton in some compounds with diverse biological activities. In this work, an efficient diastereoselective 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ from 3-amino oxindoles and aldehydes with maleimides has been described. The protocol provides a facile and efficient access to structurally diverse succinimide-fused spiro[pyrrolidine-2,3′-oxindole] compounds in good to high yields (up to 93%) with moderate to excellent diastereoselectivities (up to >95:5). The relative stereochemistry of cycloaddition products has been assigned by X-ray diffraction analysis.
Highlights
The spiro[pyrrolidine-2,30 -oxindole] has been identified as the core structural skeleton in some unnaturalThe compounds with diverse biologicalhas activities [1,2,3,4,5,6]
Most studies have focused on 1,3-dipolar cycloaddition of azomethine ylides generated condensation isatins amino azomethine ylides generatedininsitu situvia viadecarboxylative decarboxylative condensation of of isatins withwith amino acidsacids
We describe a facile and efficient strategy for accessing to succinimide-fused spiro[pyrrolidine-2,3′-oxindoles] by a one-pot three-component 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ from 3-amino oxindoles 1 and aldehydes with maleimides 3 in the presence of triethylamine (TEA, Scheme 1c), which is a supplement to Molecules 2018, 23, 582 previous work
Summary
The spiro[pyrrolidine-2,30 -oxindole] has been identified as the core structural skeleton in some unnaturalThe compounds with diverse biologicalhas activities [1,2,3,4,5,6]. Been attracting recent discovery of some important biological activities such has as anti-tumor [7], more. Much more attention has to developing synthetic strategies toward the construction of this spirocyclic structure [2,7,9,10,11,12,13,14,15,16]. Been paid to developing synthetic strategies toward the construction of this spirocyclic structure. Among these reported approaches, most studies have focused on 1,3-dipolar cycloaddition of [2,7,9,10,11,12,13,14,15,16]. Most studies have focused on 1,3-dipolar cycloaddition of azomethine ylides generated condensation isatins amino azomethine ylides generatedininsitu situvia viadecarboxylative decarboxylative condensation of of isatins withwith amino acidsacids
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