Oxidative photochemical cyclization of ethyl 3-(indol-3-yl)-3-oxo-2-phenylpropanoate derivatives: synthesis of benzo[a]carbazoles

被引：14
|
作者：
Li, Yinlong [1 ]
Pang, Zhonghua [1 ]
Zhang, Tianqi [1 ]
Yang, Jidong [1 ]
Yu, Wei [1 ]
机构：
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
TETRAHEDRON | 2015年 / 71卷 / 21期
基金：
中国国家自然科学基金;
关键词：
Photocyclization; Benzo[a]carbazole; Ethyl 3-(1-methyl-1H-indol-3-yl)-3-oxopropanoates; Ullmann-Hurtley reaction; CATALYZED ALPHA-ARYLATION; COUPLING REACTIONS; C-N; ARYL HALIDES; COPPER; ULLMANN; PHOTOCYCLIZATION; ANNULATION; ALKALOIDS; CHEMISTRY;
D O I：
10.1016/j.tet.2015.03.107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
6-Ethoxycarbonyl-5-hydroxy-benzo[a]carbazoles were prepared from ethyl 3-(1-methyl-1H-indol-3-yl)-3-oxopropanoates in two steps: the first step involved alpha-arylation of the indicated starting materials via Ullmann-Hurtley reaction; in the key second step, the thus formed coupling products underwent oxidative photocyclization to afford the benzo[a]carbazole ring. The present photocyclization features the use of CuBr2 to prompt the transformations, which could not be realized under the conventional conditions. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3351 / 3358
页数：8
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