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通过无催化剂氮杂迈克尔加成/C(sp)-O键形成串联反应构建 - 二茂铁取代苯并二氢恶唑

Construction of -Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp)-O Bond Formation Tandem Reaction.

作者信息

Zhang Mingliang, Zhao Pin, Liu Qilv, Liu Xinlei, Hu Jingya, Wu Dongqing, Liu Lantao

机构信息

Henan Engineering Research Center of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China.

College of Chemistry, Zhengzhou University, Zhengzhou 450052, China.

出版信息

Molecules. 2023 Jul 24;28(14):5615. doi: 10.3390/molecules28145615.

DOI:10.3390/molecules28145615
PMID:37513488
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10384804/
Abstract

A catalyst-free aza-Michael addition/C(sp)-O bond formation tandem reaction of substituted amino ferrocenes with quinone esters was developed, which provided a green and efficient strategy for the construction of a C(sp)-O bond from C(sp)-H, and a series of -ferrocene-substituted benzodihydrooxazoles were smoothly produced in moderate to excellent yields (up to >99% yield). The mechanism experiments showed that quinone esters performed as both substrate and oxidant. The salient features of this transformation include good functional group tolerance, broad substrate scope and mild conditions.

摘要

开发了一种取代氨基二茂铁与醌酯的无催化剂氮杂-Michael加成/C(sp)-O键形成串联反应,该反应为从C(sp)-H构建C(sp)-O键提供了一种绿色高效的策略,并且一系列二茂铁取代的苯并二氢恶唑以中等至优异的产率顺利生成(产率高达>99%)。机理实验表明醌酯兼具底物和氧化剂的作用。该转化反应的显著特点包括良好的官能团耐受性、广泛的底物范围和温和的反应条件。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/2121075c1fd4/molecules-28-05615-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/12072ffb987d/molecules-28-05615-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/82d576ea1989/molecules-28-05615-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/9b9eaa846ef2/molecules-28-05615-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/2121075c1fd4/molecules-28-05615-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/12072ffb987d/molecules-28-05615-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/82d576ea1989/molecules-28-05615-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/9b9eaa846ef2/molecules-28-05615-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b35/10384804/2121075c1fd4/molecules-28-05615-g001.jpg

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本文引用的文献

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Chem Soc Rev. 2023 Apr 3;52(7):2391-2479. doi: 10.1039/d0cs01466d.
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Brønsted Acid-Catalyzed Reaction of -arylnaphthalen-2-amines with Quinone Esters for the Construction of Carbazole and C-N Axially Chiral Carbazole Derivatives.布朗斯特酸催化 - 芳基萘-2-胺与醌酯的反应,用于构建咔唑和 C-N 轴向手性咔唑衍生物。
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基于二茂铁的异羟肟酸作为选择性组蛋白去乙酰化酶6抑制剂的合成及生物活性评价
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