Gold-catalyzed cascade C-C and C-N bond formation: synthesis of polysubstituted indolequinones and pyrroles

被引：36

作者：

Abdukader, Ablimit ^{[1
,2
]}

Xue, Qicai ^{[1
]}

Lin, Aijun ^{[1
]}

Zhang, Ming ^{[1
]}

Cheng, Yixiang ^{[1
]}

Zhu, Chengjian ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China

[2] Xinjiang Univ, Sch Chem & Chem Engn, Urumqi 830046, Peoples R China

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 44期

基金：

高等学校博士学科点专项科研基金;

关键词：

Gold catalysis; Cascade reaction; Pyrrole; Indolequinone; Enamine; FREE-RADICAL REACTIONS; EFFICIENT APPROACH; CARBONYL-COMPOUNDS; 2-AMINO-1,4-NAPHTHOQUINONES; INHIBITORS; ALKALOIDS; DERIVATIVES; CYCLIZATION; HETEROATOM; OXIDANT;

D O I：

10.1016/j.tetlet.2013.08.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The combination of Ph3PAuCl and AgoTf was proven to be an efficient catalyst for the cascade C-C and C-N bond formation reactions from enamines and bromoquinones or nitroolefins. This protocol affords a straightforward method for the synthesis of polysubstituted indolequinones and pyrroles in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5898 / 5900

页数：3

共 49 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2]

[Anonymous], MOD HETEROCYCL CHEM

[3] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[4]

Barber D. M., 2011, J CHEM SOC CHEM COMM, P4379

[5] Synthesis, cytotoxic activities and structure-activity relationships of topoisomerase I inhibitors: Indolizinoquinoline-5,12-dione derivatives [J].

Cheng, Yu ;

An, Lin-Kun ;

Wu, Ning ;

Wang, Xiao-Dong ;

Bu, Xian-Zhang ;

Huang, Zhi-Shu ;

Gu, Lian-Quan .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (08) :4617-4625

[6] A novel oxidative free radical reaction between 2-hydroxy-1,4-naphthoquinone and β-enamino carbonyl compounds [J].

Chuang, CP ;

Wu, YL .

TETRAHEDRON LETTERS, 2001, 42 (09) :1717-1719

[7] Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:Quinone oxidoreductase 1 (NQO1) activity [J].

Colucci, Marie A. ;

Reigan, Philip ;

Siegel, David ;

Chilloux, Aurelie ;

Ross, David ;

Moody, Christopher J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (23) :5780-5789

[8] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

[9] Gold-Catalyzed Cyclization of Alkynylaziridines as an Efficient Approach toward Functionalized N-Phth Pyrroles [J].

Du, Xiangwei ;

Xie, Xin ;

Liu, Yuanhong .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (02) :510-513

[10] Multicomponent reactions for the synthesis of pyrroles [J].

Estevez, Veronica ;

Villacampa, Mercedes ;

Carlos Menendez, J. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4402-4421

← 1 2 3 4 5 →