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

作者：Jin, Lunqiang; Liang, Feng^*

来源：Molecules, 2018, 23(3): 582.

DOI：10.3390/molecules23030582

• 1,3-dipolar cycloaddition
• azomethine ylide
• one pot synthesis
• maleimide
• succinimide-fused spiro[pyrrolidine-2,3 '-oxindole]

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.

• 出版日期2018-3
• 单位武汉科技大学