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

• Published in: Molecules (Basel, Switzerland) Switzerland), 2018-03, Vol.23 (3), p.582
• Main Authors: Jin, Lunqiang, Liang, Feng
• Format: Article
• Language: English
• Subjects: 1,3-dipolar cycloaddition; Aldehydes; Aldehydes - chemistry; Amino acids; Azo Compounds - chemistry; azomethine ylide; Chemical engineering; Chemistry Techniques, Synthetic; Construction; Cycloaddition; Cycloaddition Reaction; Indoles - chemical synthesis; Laboratories; maleimide; Maleimides - chemistry; Metallurgy; Molecular Structure; one pot synthesis; Pyrrolidine; Pyrrolidines - chemical synthesis; Solvents; Spiro Compounds - chemical synthesis; Stereochemistry; Stereoisomerism; Stereoselectivity; Succinimide; succinimide-fused spiro[pyrrolidine-2,3′-oxindole]; Succinimides - chemistry; Thiosemicarbazones - chemistry; X-ray diffraction
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules23030582

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.