| 铜催化对亚甲基苯醌/偶氮试剂/水三组分反应合成苯并呋喃-2-酮类化合物 |
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| 引用本文： | 盛回香,余健,王硕文,徐振华,唐石.铜催化对亚甲基苯醌/偶氮试剂/水三组分反应合成苯并呋喃-2-酮类化合物[J].应用化学,2019,36(11):1266-1274. |
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| 作者姓名： | 盛回香 余健 王硕文 徐振华 唐石 |
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| 作者单位： | 吉首大学化学化工学院,武陵山民族药解析与创制湖南省工程实验室 湖南 吉首 416000 |
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| 基金项目： | 国家自然基金(21462017)、吉首大学湖南省大学生研究性学习和创新性实验项目(JGCX2018149)资助 |
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| 摘 要： | 发展了一种高效、简便的潜在生物活性的含氰苯并呋喃-2-酮类化合物的合成新方法。 以廉价碘化亚酮为催化剂,锌粉为添加剂,催化对亚甲基苯醌与1,1-偶氮双(环己烷甲腈)和H2O三组分反应,经历1,6-共轭加成/芳构化,惰性碳-碳键断裂,以及后续的串联自由基插氰/环化及水解等步骤,“一锅法”快速合成了一系列含氰苯并呋喃酮结构的化合物。 为含氰苯并呋喃酮类化合物的合成提供一条简便而高效的途径,同时也为对亚甲基苯醌类化合物的高值化应用提供一个新的思路。
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| 关 键 词： | C—C键官能化 1 1-偶氮双(环己烷甲腈) 铜催化 苯并呋喃酮 对亚甲基苯醌 |
| 收稿时间： | 2019-03-25 |
Copper-Catalyzed Three-Component Synthesis of Benzofuran-2-one from para-Quinone Methides/Azo Reagent/H2O |
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| SHENG Huixiang,YU Jian,WANG Shuowen,XU Zhenhua,TANG Shi.Copper-Catalyzed Three-Component Synthesis of Benzofuran-2-one from para-Quinone Methides/Azo Reagent/H2O[J].Chinese Journal of Applied Chemistry,2019,36(11):1266-1274. |
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| Authors: | SHENG Huixiang YU Jian WANG Shuowen XU Zhenhua TANG Shi |
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| Institution: | Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wuling ountains,College of Chemistry and Chemical Engineering Jishou University,Hunan,Jishou 416000,China |
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| Abstract: | A new and efficient method for the synthesis of potentially biologically active cyano-containing benzofuran-2-one derivatives has been developed. In the presence of low-cost CuI and zinc powder, the three-component reactions of para-quinone methides with 1,1-azobis(cyclohexanecarbonitrile) and H2O proceed smoothly through radical cascades, including 1,6-conjugate addition/aromatization, inert C(aryl)—C(t-butyl) bond cleavage and downstream cyano-insertion/cyclization/hydrolysis, which leads to a series of cyano-containing benzofuran-2-ones. This method offers a simple and efficient way for the synthesis of cyano-containing benzofuranone derivatives, as well as a new idea for the high-value application of para-quinone methides. |
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| Keywords: | C—C bond functionalization 1 1'-azobis(cyanocyclohexane) copper catalysis benzofuranone para-quinone methides |
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