Copper-catalyzed synthesis of 2,3-disubstituted indoles from ortho-haloanilines and β-keto esters/β-diketone

被引：20

作者：

Liu, Xiao-Guang ^{[1
]}

Li, Zi-Hao ^{[1
]}

Xie, Jian-Wei ^{[1
]}

Liu, Ping ^{[1
]}

Zhang, Jie ^{[1
]}

Dai, Bin ^{[1
]}

机构：

[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, North 4th Rd, Shihezi 832003, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 05期

关键词：

2,3-Disubstituted indoles; Copper; Domino reaction; Tetrazole-1-acetic acid; ortho-Haloanilines; N-ARYLATION; TETRAZOLE-1-ACETIC ACID; POLYSUBSTITUTED INDOLES; CRYSTAL-STRUCTURE; ARYL IODIDES; ALKALOIDS; DERIVATIVES; IMIDAZOLES; ANNULATION; POLYMERS;

D O I：

10.1016/j.tet.2015.12.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrazole-1-acetic acid was identified as an efficient ligand to promote copper-catalyzed domino reaction of ortho-iodo/bromo-anilines with beta-keto esters/beta-diketone for 2,3-disubstituted indoles' synthesis with high yields under mild conditions. The protocol, with easy-available catalytic system, shows good substrate tolerance towards various functional groups. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：653 / 657

页数：5

共 28 条

[1] Domino Ligand-Free Copper-Catalyzed Synthesis of Polysubstituted Indoles [J].

Ali, Md Ashif ;

Punniyamurthy, Tharmalingam .

SYNLETT, 2011, (05) :623-626

[2] Applications of Bartoli indole synthesis [J].

Bartoli, Giuseppe ;

Dalpozzo, Renato ;

Nardi, Monica .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4728-4750

[3]

Bronner SM, 2011, HETEROCYCLES IN NATURAL PRODUCT SYNTHESIS, P221

[4] Elaboration of 2-(trifluoromethyl)indoles via a cascade coupling/condensation/deacylation process [J].

Chen, Yu ;

Wang, Yuji ;

Sun, Zheming ;

Ma, Dawei .

ORGANIC LETTERS, 2008, 10 (04) :625-628

[5] Facile access to polysubstituted Indoles via a cascade Cu-catalyzed arylation - Condensation process [J].

Chen, Yu ;

Xie, Xiaoan ;

Ma, Dawei .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9329-9334

[6] Synthesis of Indole Derivatives via Domino Reactions [J].

Feng, Yadong ;

Zhang, Hong ;

Cheng, Guolin ;

Cui, Xiuling .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (08) :1499-1508

[7]

Fischer E., BER DTSCH CHEM GES, V16, P2241, DOI [DOI 10.1002/CBER.188301602141, 10.1002/cber.188301602141]

[8] Indole synthesis through transition metal-catalyzed C-H activation [J].

Guo, Tenglong ;

Huang, Fei ;

Yu, Likun ;

Yu, Zhengkun .

TETRAHEDRON LETTERS, 2015, 56 (02) :296-302

[9] Synthesis of indole and its derivatives in water [J].

Gupta, Neeraj ;

Goyal, Deepti .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (01) :4-16

[10] A Simple and Efficient Copper(II) Complex as a Catalyst for N-Arylation of Imidazoles [J].

Jiao, Yanli ;

Yan, Nannan ;

Xie, Jianwei ;

Ma, Xiaowei ;

Liu, Ping ;

Dai, Bin .

CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (02) :267-270

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