Base-mediated [4+2] annulation of electron-deficient nitrobenzoheterocycles and alpha,alpha-dicyanoalkenes in water: Facile access to structurally diverse functionalized dibenzoheterocyclic compounds
Base-mediated [4+2] annulation of electron-deficient nitrobenzoheterocycles and alpha,alpha-dicyanoalkenes in water: Facile access to structurally diverse functionalized dibenzoheterocyclic compounds
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水中缺电子硝基苯并杂环和α,α-二氰基烯烃的碱介导[4 2]成环：轻松获得结构多样的官能化二苯并杂环化合物
DOI：
10.1016/j.tet.2020.131115
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发表时间：
2020
期刊：
影响因子：
2.1
通讯作者：
Yuan Wei-Cheng
中科院分区：
文献类型：
--
作者：
Zhuo Jun-Rui;Quan Bao-Xue;Zhao Jian-Qiang;Zhang Ming-Liang;Chen Yong-Zheng;Zhang Xiao-Mei;Yuan Wei-Cheng
开发了2-硝基苯并呋喃、2-硝基苯并噻吩、3-硝基苯并噻吩和3-硝基吲哚与α,α-二氰基烯烃的碱介导[4 + 2]环化，用于合成结构多样的二苯并杂环化合物。该反应以碳酸铯为碱，在水中通过串联插烯迈克尔加成/环化/互变异构/消除过程顺利进行，以良好到高的产率提供了多种二苯并呋喃、二苯并噻吩和咔唑。该方法的合成潜力通过放大实验和产品的多功能转化得到了证明。并对多杂环芳香族产物的光学性能进行了初步研究。 (C) 2020 Elsevier Ltd. 保留所有权利。
A base-mediated [4 + 2] annulation of 2-nitrobenzofurans, 2-nitrobenzothiophenes, 3-nitrobenzothiophenes, and 3-nitroindoles with a,a-dicyanoalkenes for the synthesis of structurally diverse dibenzoheterocyclic compounds was developed. The reaction proceeded smoothly via a tandem vinylogous Michael addition/cyclization/tautomerization/elimination process in water with cesium carbonate as base, affording a wide range of dibenzofurans, dibenzothiophenes and carbazoles in good to high yields. The synthetic potential of the methodology was demonstrated by the scale-up experiment and versatile transformations of the products. The optical property of the polyheterocyclic aromatic products was also preliminarily investigated. (C) 2020 Elsevier Ltd. All rights reserved.