A Cu-Catalysed Radical Cross-Dehydrogenative Coupling Approach to Acridanes and Related Heterocycles

被引：13

作者：

Hurst, Timothy E. ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

Acridanes; Copper; Homogeneous catalysis; Nitrogen heterocycles; Cross-coupling; Dehydrogenation; One-pot reaction; HYDRIDE-TRANSFER; RING-EXPANSION; N-ARYLATION; DERIVATIVES; FUNCTIONALIZATION; TEMPERATURE; OXINDOLES; PHENOLS; ANALOGS; AMINES;

D O I：

10.1002/ejoc.201601336

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of acridanes and related compounds through a Cu-catalysed radical cross-dehydrogenative coupling of simple 2-[2-(arylamino) aryl] malonates is reported. This method can be further streamlined to a one-pot protocol involving the in situ fomation of the 2-[2-(arylamino) aryl]malonate by alpha-arylation of diethyl malonate with 2-bromodiarylamines under Pd catalysis, followed by Cu-catalysed cyclisation.

引用

页码：203 / 207

页数：5

共 47 条

[41] Oxidative C-H Bond Functionalization and Ring Expansion with TMSCHN2: A Copper(I)-Catalyzed Approach to Dibenzoxepines and Dibenzoazepines [J].

Stopka, Tobias ;

Marzo, Leyre ;

Zurro, Mercedes ;

Janich, Simon ;

Wuerthwein, Ernst-Ulrich ;

Daniliuc, Constantin G. ;

Aleman, Jose ;

Mancheno, Olga Garcia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (17) :5049-5053

[42] Preparation and structure of acenaphthylene-1,2-diyldi(9-acridine) derivatives with a long C=C bond [J].

Takeda, Takashi ;

Uchimura, Yasuto ;

Kawai, Hidetoshi ;

Katoono, Ryo ;

Fujiwara, Kenshu ;

Suzuki, Takanori .

CHEMICAL COMMUNICATIONS, 2014, 50 (30) :3924-3927

[43] Diphenylmethylene hydroxamic acids as selective class IIa histone deacetylase inhibitors [J].

Tessier, Pierre ;

Smil, David V. ;

Wahhab, Amal ;

Leit, Silvana ;

Rahil, Jubrail ;

Li, Zuomei ;

Deziel, Robert ;

Besterman, Jeffrey M. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (19) :5684-5688

[44] Controlling Ring Translation of Rotaxanes [J].

Vetter, Antje ;

Abraham, Werner .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4666-4681

[45] CuI/L-proline-catalyzed coupling reactions of aryl halides with activated methylene compounds [J].

Xie, XA ;

Cai, GR ;

Ma, DW .

ORGANIC LETTERS, 2005, 7 (21) :4693-4695

[46] Room-temperature copper-catalyzed α-arylation of malonates [J].

Yip, Sau Fan ;

Cheung, Hong Yee ;

Zhou, Zhongyuan ;

Kwong, Fuk Yee .

ORGANIC LETTERS, 2007, 9 (17) :3469-3472

[47] Metal-free TEMPO-catalyzed oxidative C-C bond formation from Csp3-H bonds using molecular oxygen as the oxidant [J].

Zhang, Bo ;

Cui, Yuxin ;

Jiao, Ning .

CHEMICAL COMMUNICATIONS, 2012, 48 (37) :4498-4500

← 1 2 3 4 5 →