A unified protocol for the synthesis of chromones, thiochromones and γ-pyrones via a dehydrative rearrangement reaction at room temperature
文献类型：期刊论文
| 作者 | Wang, Yue-Qi2,3; Jin, Wei-Li2,3; Chen, Hui-Qing3; Zhou, Jin-Xin1,3; Shen, Hong-Yan3; Wang, Jie1,2,3 |
| 刊名 | ORGANIC CHEMISTRY FRONTIERS
 |
| 出版日期 | 2025-03-08 |
| 页码 | 9 |
| ISSN号 | 2052-4129 |
| DOI | 10.1039/d4qo02397h |
| 通讯作者 | Wang, Jie(jiewang@simm.ac.cn) |
| 英文摘要 | In this study, we present our discovery that a combination of dichloromethyl methyl ether (DCME) and a Lewis acid, a reaction condition traditionally used for Rieche formylation, is capable of activating 1,3-dioxin-4-ones and 1,3-oxathiin-6-ones chemoselectively at room temperature. This activation triggers an intriguing dehydrative rearrangement (DHR) reaction, yielding chromone, thiochromone and gamma-pyrone derivatives with diverse substitutions. This protocol leverages widely available starting materials and feedstock reagents, offering a mild, practical, and scalable approach that delivers products in good to excellent yields with broad functional group compatibility. In addition, kinetic studies revealed that the DCME/Lewis acid conditions preferentially facilitate the DHR reaction over Rieche formylation on electron-neutral and moderately electron-rich aromatics. The widespread availability and operational simplicity of this method bode well for its broad and rapid adoption in various applications. |
| WOS关键词 | C-H ACTIVATION ; CARBONYLATIVE SYNTHESIS ; PRIVILEGED SCAFFOLD ; ALPHA-ALKOXY ; SALICYLALDEHYDES ; ANNULATION ; ALKYNES ; FLAVONES ; CLEAVAGE ; ACETYLENES |
| 资助项目 | Strategic Priority Research Program of the Chinese Academy of Sciences[XDB1060000] ; The 1000-Youth Talents Plan ; National Natural Science Foundation of China[22101290] ; State Key Laboratory of Chemical Biology ; Shanghai Institute of Materia Medica |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001446805700001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/316674]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Wang, Jie |
| 作者单位 | 1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Yue-Qi,Jin, Wei-Li,Chen, Hui-Qing,et al. A unified protocol for the synthesis of chromones, thiochromones and γ-pyrones via a dehydrative rearrangement reaction at room temperature[J]. ORGANIC CHEMISTRY FRONTIERS,2025:9. |
| APA | Wang, Yue-Qi,Jin, Wei-Li,Chen, Hui-Qing,Zhou, Jin-Xin,Shen, Hong-Yan,&Wang, Jie.(2025).A unified protocol for the synthesis of chromones, thiochromones and γ-pyrones via a dehydrative rearrangement reaction at room temperature.ORGANIC CHEMISTRY FRONTIERS,9. |
| MLA | Wang, Yue-Qi,et al."A unified protocol for the synthesis of chromones, thiochromones and γ-pyrones via a dehydrative rearrangement reaction at room temperature".ORGANIC CHEMISTRY FRONTIERS (2025):9. |
入库方式： OAI收割
来源：上海药物研究所
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