Construction of Spiro Pyrrolidine Oxindoles Bearing Thiochromen-4-one via Domino Decarboxylation and 1,3-Dipolar Cycloaddition

doi:10.6023/cjoc202604038

Chinese Journal of Organic Chemistry

ARTICLE

基于脱羧串联与1,3-偶极环加成反应构建含硫色烯-4-酮的螺吡咯烷酮吲哚类化合物

冯振宇^a, 李霞^a,*, 钟锦林^b, 张舜光^a,*

^a天津市有机太阳能电池与光化学转换重点实验室天津理工大学化学化工学院天津 300834;
^b烟台市特种设备检验研究院烟台 265500

收稿日期:2026-04-24 修回日期:2026-07-20

Construction of Spiro Pyrrolidine Oxindoles Bearing Thiochromen-4-one via Domino Decarboxylation and 1,3-Dipolar Cycloaddition

Zhenyu Feng^a, Xia Li^a,*, Jinlin Zhong^b, Shunguang Zhang^a,*

^aTianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384 China;
^bYantai Special Equipment Inspection and Research Institute, Ynatai, 265500

Received:2026-04-24 Revised:2026-07-20
Contact: ^* E-mail: zsgmail@163.com

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Abstract

A novel and efficient synthesis of thiochromene-containing spiro pyrrolidine oxindoles has been developed via a 1,3-dipolar cycloaddition reaction. In this transformation, (E)-2-styryl-4H-thiochromen-4-one serves as the dipolarophile, while azomethine ylides generated in situ from isatins and L-proline act as the 1,3-dipoles. Notably, the cycloaddition selectively occurs at the γ,δ-double bond remote from the electron-withdrawing carbonyl group, preserving the conjugated thiochromenone framework-a scenario rarely reported in such conjugated systems. The three-component one-pot reaction proceeds under mild conditions to afford a broad range of spirooxindoles in moderate to good yields with high regio- and chemoselectivity. The synthetic utility is demonstrated by a gram-scale experiment and subsequent derivatizations, including N-acylation and selective oxidation of the sulfur atom to the corresponding sulfoxide. This work expands the chemical space of spirooxindole-based scaffolds and provides a practical strategy for constructing sulfur-containing spiro heterocycles with potential bioactivity.

Key words: Spirooxindoles, Thiochromone, 1,3-Dipolar cycloaddition

Cite this article

Zhenyu Feng, Xia Li, Jinlin Zhong, Shunguang Zhang. Construction of Spiro Pyrrolidine Oxindoles Bearing Thiochromen-4-one via Domino Decarboxylation and 1,3-Dipolar Cycloaddition[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604038.

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基于脱羧串联与1,3-偶极环加成反应构建含硫色烯-4-酮的螺吡咯烷酮吲哚类化合物

Construction of Spiro Pyrrolidine Oxindoles Bearing Thiochromen-4-one via Domino Decarboxylation and 1,3-Dipolar Cycloaddition

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