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通过烯炔亚胺、费歇尔卡宾配合物和缺电子炔烃的三组分偶联合成高度取代的苯环体系。

Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines, Fischer carbene complexes, and electron-deficient alkynes.

作者信息

Dhakal Bishnu, Gamage Lalith S R, Zhang Yanshi, Herndon James W

机构信息

Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003 USA.

出版信息

Tetrahedron Lett. 2017 Apr 5;58(14):1403-1407. doi: 10.1016/j.tetlet.2017.02.070. Epub 2017 Feb 24.

DOI:10.1016/j.tetlet.2017.02.070
PMID:28966403
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5619673/
Abstract

Three-component coupling of Fischer carbene complexes, enyne aldehyde hydrazones, and electron-deficient alkynes leads to simple benzoate derivatives in a process involving the formation of an N-aminopyrrole derivative, Diels-Alder reaction, and nitrene extrusion. The products are readily converted into isoquinolones through reaction with primary amines. The reaction proceeds best with highly substituted and electron-rich pyrroles even though these are the sterically least favorable substrates, and this reactivity trend is supported by a computational study.

摘要

费歇尔卡宾配合物、烯炔醛腙和缺电子炔烃的三组分偶联反应,在一个涉及形成N-氨基吡咯衍生物、狄尔斯-阿尔德反应和氮烯消除的过程中生成简单的苯甲酸酯衍生物。通过与伯胺反应,产物可很容易地转化为异喹啉酮。该反应在高度取代且富电子的吡咯存在下进行得最好,尽管这些是空间位阻最不利的底物,并且这种反应活性趋势得到了计算研究的支持。

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本文引用的文献

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