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0 202604009

DOI: https://doi.org/10.6023/cjoc202604009

研究论文

有机膦催化下氨(羟)基取代的α,β-不饱和酯(酮)与异(硫)氰酸酯的[3+2]和[4+2]环加成反应

  • Hu ,
  • Yi ,
  • Cai ,
  • Yifei ,
  • Gao ,
  • Haojie ,
  • Jiang ,
  • qingge ,
  • Liu ,
  • Mingguo ,
  • Wang ,
  • Nengzhong ,
  • Huang ,
  • Nianyu
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  • 三峡大学生物与制药学院 天然产物研究与利用湖北省重点实验室 湖北宜昌 443002
†共同第一作者

收稿日期: 2026-06-16

  修回日期: 2026-07-14

  网络出版日期: 2026-08-24

基金资助

111引智基地(D20015)、湖北省自然科学基金宜昌创新发展联合基金重点项目(2025AFD262)、湖北省中央引导地方科技发展资金项目(2024BSB016).

收起

Phosphine-Catalyzed [3+2] and [4+2] Annulations of Amino(Hydroxyl)-Substituted α,β-Unsaturated Esters(Ketones) with Iso(thio)cyanates

  • 胡燚 ,
  • 蔡逸飞 ,
  • 高浩杰 ,
  • 姜磬歌 ,
  • 刘明国 ,
  • 王能中 ,
  • 黄年玉
Expand
  • Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang Hubei 443002
†These authors contributed equally to this work.

Received date: 2026-06-16

  Revised date: 2026-07-14

  Online published: 2026-08-24

Supported by

111 Project (No. D20015), the Hubei Provincial Natural Science Foundation Joint Fund for Innovation and Development Project of Yichang (2025AFD262), and the Hubei Provincial Central Government Guided Local Science and Technology Development Project (2024BSB016).

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摘要

多杂原子五、六元饱和环状化合物广泛存在于天然产物与药物分子中, 具备优良的生物活性, 其骨架构建是有机合成领域的研究热点. 目前该类不同骨架化合物需采用不同方法合成, 整体合成效率偏低. 本文报道一种通过有机膦催化下氨(羟)基取代的α,β-不饱和酯(酮)与异(硫)氰酸酯的[3+2]和[4+2]环加成反应, 实现咪(噁)唑烷(硫)酮、四氢嘧啶酮和噁嗪烷酮类化合物的多样性发散式高效合成. 该方法具有操作简便、底物适用范围广、100%原子利用率等优点. 此外, 克级规模合成及衍生化反应表明该方法具有较好的应用价值.

关键词： 有机膦催化; 环加成反应; 咪唑烷酮; 四氢嘧啶酮; 噁嗪烷酮

本文引用格式

Hu , Yi , Cai , Yifei , Gao , Haojie , Jiang , qingge , Liu , Mingguo , Wang , Nengzhong , Huang , Nianyu . 有机膦催化下氨(羟)基取代的α,β-不饱和酯(酮)与异(硫)氰酸酯的[3+2]和[4+2]环加成反应[J]. 有机化学, 0 : 202604009 . DOI: 10.6023/cjoc202604009

Abstract

Five- and six-membered saturated polyheterocyclic compounds are widely found in natural products and pharmaceuticals with excellent biological activities. These scaffolds have attracted significant attention in organic synthesis. However, constructing these scaffolds typically requires different approaches, resulting in low synthetic efficiency. This paper reports a novel method for the efficient divergent synthesis of imidazolidinones, oxazolidinones, imidazolidinethiones, oxazolidinethiones tetrahydropyrimidinones, and oxazinanones via phosphine-catalyzed [3+2] and [4+2] annulations of amino (hydroxyl)-substituted α,β-unsaturated esters (ketones) with iso(thio)cyanates. This method offers advantages such as simple operation, broad substrate scope, and 100% atom economy. Gram-scale synthesis and further transformations demonstrate its good application potential.

Key words： phosphine catalysis; annulation; imidazolidinone; tetrahydropyrimidinone; oxazinanone

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