可见光驱动1,3-烯炔与4-酰基二氢吡啶的串联环化反应合成氮杂芳烃官能团化的多取代呋喃

doi:10.6023/cjoc202509014

研究论文

可见光驱动1,3-烯炔与4-酰基二氢吡啶的串联环化反应合成氮杂芳烃官能团化的多取代呋喃

王光辉^a,#, 王冰辉^b,#, 班旭^a,*, 赵筱薇^c,*, 江智勇^a,d,*

^a河南师范大学化学化工学院新乡 453007;
^b漯河医学高等专科学校河南省特医食品工程技术研究中心漯河 462000;
^c河南大学药学院开封 453007;
^d南京大学化学化工学院配位化学国家重点实验室南京 210093

收稿日期:2025-10-02 修回日期:2025-10-28
基金资助:
国家自然科学基金(Nos. 22301061, 22171072, 22201068, 22471064, 和22401086),河南省自然科学基金重点项目(Nos. 252300421286和254000510005),河南省科学技术厅科学技术研究项目(Nos. 252102310409),漯河医学高等专科学校博士科研启动基金项目(Nos. 2024-DF-04)和南京大学化学化工学院配位化学国家重点实验室开放研究基金资助.

Visible Light-Driven Tandem Cyclization Reactions of 1,3-Eneynes with 4-Acyl-Dihydropyridines to Access Azaarene-Functionalized Polysubstituted Furans

Guanghui Wang^a,#, Binghui Wang^b,#, Xu Ban^a,*, Xiaowei Zhao^c,*, Zhiyong Jiang^a,d,*

^aSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, China 453007;
^bHenan Province Engineering & Technology Research Center of Foods for Special Medical Purpose, Luohe Medical College, Luohe, China 462000;
^cCollege of Pharmacy, Henan University, Jinming Campus, Kaifeng, Henan, China 475004;
^dState Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China 210093

Received:2025-10-02 Revised:2025-10-28
Contact: *E-mail: banxu@htu.edu.cn; rosamary0530@sina.com; jiangzhiyong@htu.edu.cn
About author:^#The authors contributed equally to this work
Supported by:
National Science Foundation of China (Nos. 22301061, 22171072, 22201068, 22471064, and 22401086), the Key Project of the Henan Provincial Natural Science Foundation (Nos. 252300421286 and 254000510005), the Science and Technology Research Project of Henan Provincial Department of Science and Technology (Nos. 252102310409), the Doctoral Scientific Research Start-Up Foundation of Luohe Medical College (Nos. 2024-DF-04), and Open Research Fund of State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University.

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摘要/Abstract

本文建立了一种可见光驱动、Brønsted酸促进的1,3-烯炔与4-酰基-1,4-二氢吡啶（4-acyl-DHPs）串联环化反应,实现了氮杂芳烃官能团化的多取代呋喃的高效合成。该无金属合成策略在温和条件下进行,具有较广的底物适用范围,可兼容含有复杂药物结构的烯炔底物及多种酰基自由基前体。机理研究表明,反应经历了自由基-阴离子-质子化的连续过程,包含酰基自由基加成、联烯中间体形成以及Brønsted酸促进的环异构化过程。该方法具有模块化和环境友好的特点,可高效构筑含杂芳烃片段的多功能化呋喃,并表现出优异的官能团耐受性。

关键词: 可见光, 光反应, 多取代呋喃, 串联反应, 1,3-烯炔

A visible-light-driven, Brønsted-Lowry acids-promoted cascade cyclization between 1,3-enynes and 4-acyl-1,4-dihydropyridines (4-acyl-DHPs) has been established for the efficient synthesis of azaarene-functionalized polysubstituted furans. This metal-free transformation proceeds under mild reaction conditions and exhibits a broad substrate scope, encompassing complex drug-derived enynes and diverse acyl radical precursors. Mechanistic investigations support a reaction pathway involving a radical-anionic-protonation sequence, including acyl radical addition, allene formation, and Brønsted-Lowry acids-facilitated cycloisomerization. The methodology offers a modular and environmentally benign route to azaarene-containing, densely functionalized furans with excellent functional group compatibility.

Key words: visible light, photochemical synthesis, poly-substituted furan, cascade reaction, 1,3-eneynes

引用此文

王光辉, 王冰辉, 班旭, 赵筱薇, 江智勇. 可见光驱动1,3-烯炔与4-酰基二氢吡啶的串联环化反应合成氮杂芳烃官能团化的多取代呋喃[J]. 有机化学, doi: 10.6023/cjoc202509014.

Guanghui Wang, Binghui Wang, Xu Ban, Xiaowei Zhao, Zhiyong Jiang. Visible Light-Driven Tandem Cyclization Reactions of 1,3-Eneynes with 4-Acyl-Dihydropyridines to Access Azaarene-Functionalized Polysubstituted Furans[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202509014.

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