PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles

被引：23

作者：

Chaisan, Nattawadee ^{[1
]}

Kaewsri, Wilailak ^{[1
]}

Thongsornkleeb, Charnsak ^{[1
,2
]}

Tummatorn, Jumreang ^{[1
,3
]}

Ruchirawat, Somsak ^{[1
,3
]}

机构：

[1] Minist Educ, Ctr Excellence Environm Hlth & Toxicol EHT, Chulabhorn Grad Inst, Program Chem Biol, 54 Kamphaeng Phet 6, Bangkok 10210, Thailand

[2] Chulabhorn Res Inst, Lab Organ Synth, 54 Kamphaeng Phet 6, Bangkok 10210, Thailand

[3] Chulabhorn Res Inst, Lab Med Chem, 54 Kamphaeng Phet 6, Bangkok 10210, Thailand

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 07期

关键词：

Indoles; 2-Alkynylanilines; Catalysis; Hydroamination; Cyclization; ALCOHOLS; ALKENES; ALKYNES; REARRANGEMENT; DERIVATIVES; CASCADE; ESTERS;

D O I：

10.1016/j.tetlet.2018.01.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1-2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：675 / 680

页数：6

共 19 条

[1] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409

[2] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[3] Mechanism of the Platinum(II)-Catalyzed Hydroamination of 4-Pentenylamines [J].

Bender, Christopher F. ;

Brown, Timothy J. ;

Widenhoefer, Ross A. .

ORGANOMETALLICS, 2016, 35 (02) :113-125

[4] Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides with allyl esters. A regioselective synthesis of 3-allylindoles [J].

Cacchi, S ;

Fabrizi, G ;

Pace, P .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1001-1011

[5] Electrophilic activation of alkenes by platinum(II):: So much more than a slow version of palladium(II) [J].

Chianese, Anthony R. ;

Lee, Stephen J. ;

Gagne, Michel R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4042-4059

[6] One-Pot Synthesis of Highly Substituted 4-Acetonylindoles via Sequential Dearomatization and Silver-Catalyzed Domino Reaction [J].

Feng, Xin ;

Wang, Huiqing ;

Yang, Bo ;

Fan, Renhua .

ORGANIC LETTERS, 2014, 16 (13) :3600-3603

[7] Platinum- and gold-catalyzed rearrangement reactions of propargyl acetates:: Total syntheses of (-)-α-cubebene, (-)-cubebol, sesquicarene and related terpenes [J].

Fürstner, A ;

Hannen, P .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (11) :3006-3019

[8] The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles [J].

Janreddy, Donala ;

Kavala, Veerababurao ;

Kuo, Chun-Wei ;

Kuo, Ting-Shen ;

He, Chiu-Hui ;

Yao, Ching-Fa .

TETRAHEDRON, 2013, 69 (15) :3323-3330

[9] PtCl4-Catalyzed Cyclization Reaction of β-Allenols in the Presence of Indoles [J].

Kong, Wangqing ;

Cui, Jie ;

Yu, Yihua ;

Chen, Guofei ;

Fu, Chunling ;

Ma, Shengming .

ORGANIC LETTERS, 2009, 11 (06) :1213-1216

[10] Platinum-Catalyzed Synthesis of Substituted Phenanthrenes from Biphenyl Propargyl Alcohols via a Carbene Intermediate [J].

Kwon, Yongseok ;

Kim, Illan ;

Kim, Sanghee .

ORGANIC LETTERS, 2014, 16 (18) :4936-4939

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