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2025 , Vol. 45 >Issue 4: 1369 - 1378

DOI: https://doi.org/10.6023/cjoc202406026

研究论文

β-二羰基化合物与靛红衍生的α,β-不饱和酮之间的Michael加成/半缩酮化串联反应构建3,4'-吡喃-螺环氧化吲哚类化合物

  • 张明美 ,
  • 沙风 ,
  • 伍新燕
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  • 华东理工大学化学与分子工程学院 结构可控先进功能材料及其制备教育部重点实验室 上海 200237

收稿日期: 2024-06-20

  修回日期: 2024-09-15

  网络出版日期: 2024-10-11

基金资助

海拙道投资管理有限公司资助项目

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Michael Addition/Hemiketalization Cascade Reaction Between β-Dicarbonyl Compounds and Isatin-Derived α,β-Unsaturated Ketones to Construct 3,4'-Pyran-spirooxindoles

  • Mingmei Zhang ,
  • Feng Sha ,
  • Xin-Yan Wu
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  • Key Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237
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Received date: 2024-06-20

  Revised date: 2024-09-15

  Online published: 2024-10-11

Supported by

Shanghai Zhuodao Investment Management Co., Ltd.

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摘要

3,4'-吡喃-螺环氧化吲哚结构单元存在于一些天然产物和具有生物活性的合成化合物中, 而多官能团化3,4'-吡喃-螺环氧化吲哚的合成鲜有文献报道. 本工作发展了一种4-二甲氨基吡啶(DMAP)催化作用下β-二羰基化合物与靛红衍生的α,β-不饱和酮之间的Michael加成/半缩酮化串联反应, 在温和条件下, 以最高99%的产率和大于20∶1的非对映选择性成功地合成了一系列多官能团化3,4'-吡喃-螺环氧化吲哚类化合物. 该研究为高效构建多官能团化的3,4'-吡喃-螺环氧吲哚类化合物提供了一个简单、温和的方法.

关键词： 串联反应; 催化; Michael加成; 吡喃; 螺环氧化吲哚

本文引用格式

张明美 , 沙风 , 伍新燕 . β-二羰基化合物与靛红衍生的α,β-不饱和酮之间的Michael加成/半缩酮化串联反应构建3,4'-吡喃-螺环氧化吲哚类化合物[J]. 有机化学, 2025 , 45(4) : 1369 -1378 . DOI: 10.6023/cjoc202406026

Abstract

3,4'-Pyran-spirooxindole is a structural unit existing in many natural products and bioactive synthetic compounds. The synthesis of multifunctionalized 3,4'-pyran-spirooxindole derivatives has rarely been reported. Herein a Michael addition/hemiketalization cascade reaction between β-dicarbonyl compounds and isatin-derived α,β-unsaturated ketones catalyzed by 4-dimethylaminopyridine (DMAP) is presented. A variety of multifunctionalized 3,4'-pyran-spirooxindoles were obtained in high yields (up to 99%) with excellent diastereoselectivities (dr>20∶1) under mild conditions. This methodology provides a simple and convenient method for the syntheses of multifunctionalized 3,4'-pyran-spirooxindoles.

Key words： cascade reaction; catalysis; Michael addition; pyran; spirooxindole

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