Cu(I)-/Base-Mediated Domino [5+3+1] Annulation for Highly π-Extended Carbazole Frameworks and DFT Mechanistic Insights

被引：30

作者：

Poudel, Tej Narayan ^{[1
]}

Karanjit, Sangita ^{[2
]}

Khanal, Hari Datta ^{[1
]}

Tamargo, Ramuel John Inductivo ^{[1
]}

Lee, Yong Rok ^{[1
]}

机构：

[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 38541, South Korea

[2] Univ Tokushima, Grad Sch Pharmaceut Sci, 1-78-1 Shomachi, Tokushima 7708505, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 18期

基金：

新加坡国家研究基金会;

关键词：

SUBSTITUTED CARBAZOLES; BOND FORMATION; ALKALOIDS; BENZANNULATION; CONSTRUCTION; DERIVATIVES; MIGRATION;

D O I：

10.1021/acs.orglett.8b02363

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of highly pi-extended carbazoles is described via an unexpected domino [5 + 3 + 1] annulation approach. The Cu(I)-/base-promoted reactions of 2-nitrocinnamaldehydes with benzyl cyanides provide diverse benzo[b]carbazoles. The reaction is proposed to proceed via a sequential Michael addition/intramolecular addition of an enol into a nitro group, 6 pi- electrocyclization, and the final oxidative aromatization as supported by density functional theory calculations. Some of the synthesized carbazoles showed significant potential in fluorescence sensing of Cu2+ ions.

引用

页码：5648 / 5652

页数：5