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Molecules 2018, 23(3), 582; https://doi.org/10.3390/molecules23030582

A Facile One-Pot Construction of Succinimide-Fused Spiro[Pyrrolidine-2,3′-Oxindoles] via 1,3-Dipolar Cycloaddition Involving 3-Amino Oxindoles and Maleimides

The State Key Laboratory of Refractories and Metallurgy, Coal Conversion and New Carbon Materials Hubei Key Laboratory, School of Chemistry & Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, China
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Received: 9 February 2018 / Revised: 27 February 2018 / Accepted: 1 March 2018 / Published: 5 March 2018
(This article belongs to the Special Issue Advances in Spiro Compounds)
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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. View Full-Text
Keywords: 1,3-dipolar cycloaddition; azomethine ylide; one pot synthesis; maleimide; succinimide-fused spiro[pyrrolidine-2,3′-oxindole] 1,3-dipolar cycloaddition; azomethine ylide; one pot synthesis; maleimide; succinimide-fused spiro[pyrrolidine-2,3′-oxindole]
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Jin, L.; Liang, F. A Facile One-Pot Construction of Succinimide-Fused Spiro[Pyrrolidine-2,3′-Oxindoles] via 1,3-Dipolar Cycloaddition Involving 3-Amino Oxindoles and Maleimides. Molecules 2018, 23, 582.

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