Sequential Silver-Catalyzed Oxidative Cyclization Reactions of Unprotected 2-Alkynylanilines to Anthranils

被引：18

作者：

Arcadi, Antonio ^{[1
]}

Chiarini, Marco ^{[2
]}

Del Vecchio, Luana ^{[1
,3
]}

Marinelli, Fabio ^{[1
]}

Michelet, Veronique ^{[3
]}

机构：

[1] Univ Aquila, Dipartimento Sci Fis & Chim, Via Vetoio, I-671010 Coppito, AQ, Italy

[2] Univ Teramo, Fac Biosci & Tecnol Agroalimentari & Ambientali, Via R Balzarini 1, I-64100 Teramo, Te, Italy

[3] PSL Res Univ, Chim ParisTech CNRS, Inst Rech Chim Paris, 11 Rue P&M Curie, F-75005 Paris, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 16期

关键词：

Alkynes; Anthranils; Oxidation; Cyclization; Silver; Domino reactions; EFFICIENT SYNTHESIS; CASCADE CYCLIZATION; ORTHO-ALKYNYLANILINES; METAL-FREE; INDOLES; 2-ETHYNYLANILINES; DERIVATIVES; OXONE; CYCLOISOMERIZATION; CONSTRUCTION;

D O I：

10.1002/ejoc.201601600

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The full details of the original Ag-catalyzed domino oxidative cyclization reactions of unprotected 2-alkynylanilines with Oxone are described. The influences of several parameters including the substrate features, oxidant, reaction conditions, and catalyst on the reaction outcome were explored. A plausible mechanism is provided for the unusual silver-catalyzed oxidative cyclization reactions of 2-alkynylanilines to anthranils.

引用

页码：2214 / 2222

页数：9

共 96 条

[1] Synthesis of Indole Derivatives from 2-Alkynylanilines by Means of Gold Catalysis [J].

Abbiati, Giorgio ;

Marinelli, Fabio ;

Rossi, Elisabetta ;

Arcadi, Antonio .

ISRAEL JOURNAL OF CHEMISTRY, 2013, 53 (11-12) :856-868

[2] An alternative one-pot gold-catalyzed approach to the assembly of 11H-indolo[3,2-c]quinolines [J].

Abbiati, Giorgio ;

Arcadi, Antonio ;

Chiarini, Marco ;

Marinelli, Fabio ;

Pietropaolo, Emanuela ;

Rossi, Elisabetta .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (38) :7801-7808

[3] Sequential alkylation/cyclization/isomerization of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic esters: a new route to 2-acyl- and 2-ethoxycarbonyl-3-alkenyl indoles [J].

Ambrogio, Ilaria ;

Arcadi, Antonio ;

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella ;

Marinelli, Fabio .

TETRAHEDRON, 2013, 69 (45) :9494-9498

[4]

[Anonymous], 2013, ANGEW CHEM-GER EDIT

[5] Silver-versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone [J].

Arcadi, A. ;

Chiarini, M. ;

Del Vecchio, L. ;

Marinelli, F. ;

Michelet, V. .

CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1458-1461

[6] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1989, 30 (19) :2581-2584

[7] Bronsted Acid Catalyzed Cascade Reactions of 2-[(2-Aminophenyl)ethynyl]phenylamine Derivatives with Aldehydes: A New Approach to the Synthesis of 2,2′-Disubstituted 1H,1′H-3,3′-Biindoles [J].

Arcadi, Antonio ;

Chiarini, Marco ;

D'Anniballe, Gaetano ;

Marinelli, Fabio ;

Pietropaolo, Emanuela .

ORGANIC LETTERS, 2014, 16 (06) :1736-1739

[8] Aminofluorination of 2-alkynylanilines: a Au-catalyzed entry to fluorinated indoles [J].

Arcadi, Antonio ;

Pietropaolo, Emanuela ;

Alvino, Antonello ;

Michelet, Veronique .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :449-458

[9] One-Pot Gold-Catalyzed Aminofluorination of Unprotected 2-Alkynylanilines [J].

Arcadi, Antonio ;

Pietropaolo, Emanuela ;

Alvino, Antonello ;

Michelet, Veronique .

ORGANIC LETTERS, 2013, 15 (11) :2766-2769

[10] 2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions [J].

Arcadi, Antonio ;

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella ;

Iazzetti, Antonia ;

Marinelli, Fabio .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (04) :545-548

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