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

doi:10.6023/cjoc202604009

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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

胡燚^†, 蔡逸飞^†, 高浩杰^†, 姜磬歌, 刘明国, 王能中^*, 黄年玉^*

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

收稿日期:2026-06-16 修回日期:2026-07-14
作者简介:^†共同第一作者
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).

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

Hu, Yi^†, Cai, Yifei^†, Gao, Haojie^†, Jiang, qingge, Liu, Mingguo, Wang, Nengzhong^*, Huang, Nianyu^*

Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang Hubei 443002

Received:2026-06-16 Revised:2026-07-14
About author:^†These authors contributed equally to this work.
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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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

Cite this article

Hu, Yi, Cai, Yifei, Gao, Haojie, Jiang, qingge, Liu, Mingguo, Wang, Nengzhong, Huang, Nianyu. Phosphine-Catalyzed [3+2] and [4+2] Annulations of Amino(Hydroxyl)-Substituted α,β-Unsaturated Esters(Ketones) with Iso(thio)cyanates[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604009.

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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

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

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