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在无过渡金属条件下,芳基炔酸酯与乙腈的氰甲基化和环化反应:3-氰甲基香豆素的合成。

Cyanomethylation and Cyclization of Aryl Alkynoates with Acetonitrile under Transition-Metal-Free Conditions: Synthesis of 3-Cyanomethylated Coumarins.

机构信息

College of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing Normal University , Nanjing 210023, China.

出版信息

J Org Chem. 2016 Nov 18;81(22):11489-11495. doi: 10.1021/acs.joc.6b02155. Epub 2016 Oct 31.

DOI:10.1021/acs.joc.6b02155
PMID:27768307
Abstract

Cyanomethylated coumarins were synthesized via cyanomethylation and cyclization of aryl alkynoates using cheap and available reagent acetonitrile as the cyanomethyl source in the presence of TBPB (tert-butyl peroxybenzoate) under transition-metal-free conditions. For the substrates with various substituents on benzene ring, the reaction proceeded smoothly to give the corresponding products in moderate to good yields. The resulting products could be simply converted into some other related coumarin derivatives.

摘要

氰甲基化香豆素可通过芳基炔酸酯的氰甲基化和环化反应合成,在无过渡金属条件下,使用廉价易得的试剂乙腈作为氰甲基源,在 TBPB(过氧化叔丁基苯甲酰)存在下进行。对于苯环上具有各种取代基的底物,反应顺利进行,以中等至良好的收率得到相应的产物。所得产物可简单转化为其他一些相关的香豆素衍生物。

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