DBU-mediated [4+2] annulations of donoracceptor cyclopropanes with 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines

被引：14

作者：

Liu, Jiaming ^{[1
]}

Qian, Siran ^{[1
]}

Su, Zhenjie ^{[1
]}

Wang, Cunde ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, 180 Siwangting St, Yangzhou 225002, Jiangsu, Peoples R China

来源：

RSC ADVANCES | 2017年 / 7卷 / 61期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; 1-CYANOCYCLOPROPANE; 1-ESTERS; POLYSUBSTITUTED BENZENES; STRAIGHTFORWARD APPROACH; CARBENE COMPLEXES; BENZOIC-ACID; RING; BENZANNULATION; CONSTRUCTION; STRATEGY;

D O I：

10.1039/c7ra07230a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile synthesis of fully substituted anilines by the DBU-mediated [4 + 2] annulation of donor-acceptor 1,1-dicyano-cyclopropanes with 3-aryl-2-cyanoacrylate has been developed. This reaction involves a highly efficient multiple domino sequence consisting of ring opening of donor-acceptor cyclopropanes, regioselective intermolecular Michael addition, intramolecular nucleophilic addition and aromatization as key unit steps. This transformation provides a straightforward synthetic protocol for constructing fully substituted aniline derivatives. The structure of two typical products was confirmed by X-ray crystallography.

引用

页码：38342 / 38349

页数：8

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