Gold-catalyzed synthesis of 2-substituted, 2,3-Disubstituted and 1,2,3-trisubstituted Indoles in [bmim]BF4

被引：80

作者：

Ambrogio, Ilaria

Arcadi, Antonio

Cacchi, Sandro

Fabrizi, Giancarlo

Marinelli, Fabio

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Sostanze Biologicament, I-00185 Rome, Italy

[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy

来源：

SYNLETT | 2007年 / 11期

关键词：

gold catalysis; ionic liquids; indoles; hydroamination; aza-Michael addition;

D O I：

10.1055/s-2007-982572

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of 2-alkynylanilines in the presence of NaAuCl4 center dot H2O using [bmim]BF4 as the reaction medium afforded 2substituted indoles in high yields. The catalyst system was best recycled using n-Bu(4)NAuCl4. 2,3-Disubstituted indoles could be prepared from 2-alkynylanilines and 3-buten-2-one through a one-flask annulation-alkylation sequence and 1,2,3 -trisubstituted indoles were obtained from the same starting materials via an aza-Michael addition-annulation-alkylation process.

引用

收藏

页码：1775 / 1779

页数：5

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共 53 条

[1] Synthesis of 3,3′-disubstituted-2,2′-biindolyls through sequential palladium-catalysed reactions of 2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino)-phenyl]-buta-1,3-diynyl)-phenyl)-acetamide with organic halides/triflates [J].

Abbiati, G ;

Arcadi, A ;

Beccalli, E ;

Bianchi, G ;

Marinelli, F ;

Rossi, E .

TETRAHEDRON, 2006, 62 (13) :3033-3039

[2] Solvent-free solid acid-catalyzed electrophilic annelations:: A new green approach for the synthesis of substituted five-membered N-heterocycles [J].

Abid, Mohammed ;

Spaeth, Andrew ;

Torok, Bela .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2191-2196

[3] Gold-catalyzed reactions of 2-alkynyl-phenylamines with α,β-enones [J].

Alfonsi, M ;

Arcadi, A ;

Aschi, M ;

Bianchi, G ;

Marinelli, F .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2265-2273

[4] Gold-catalyzed C-3-alkylation of 7-azaindoles through Michael-type addition to α,β-enones [J].

Alfonsi, Maria ;

Arcadi, Antonio ;

Bianchi, Gabriele ;

Marinelli, Fabio ;

Nardini, Antonella .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (10) :2393-2402

[5] Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate [J].

Ambrogio, I ;

Cacchi, S ;

Fabrizi, G .

ORGANIC LETTERS, 2006, 8 (10) :2083-2086

[6] Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles [J].

Arcadi, A ;

Bianchi, G ;

Marinelli, F .

SYNTHESIS-STUTTGART, 2004, (04) :610-618

[7] Gold-catalyzed conjugate addition type reaction of indoles with α,β-enones [J].

Arcadi, A ;

Bianchi, G ;

Chiarini, M ;

D'anniballe, G ;

Marinelli, F .

SYNLETT, 2004, (06) :944-950

[8] Cascade alkenyl amination/heck reaction promoted by a bifunctional palladium catalyst:: A novel one-pot synthesis of indoles from o-haloanilines and alkenyl halides [J].

Barluenga, J ;

Fernández, MA ;

Aznar, F ;

Valdés, C .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2276-2283

[9] Room temperature hydroamination of N-alkenyl ureas catalyzed by a gold(I) N-heterocyclic carbene complex [J].

Bender, Christopher F. ;

Widenhoefer, Ross A. .

ORGANIC LETTERS, 2006, 8 (23) :5303-5305

[10] Convenient oxidation of alkylated phenols and methoxytoluenes to antifungal 1,4-benzoquinones with hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3) catalytic system in neutral ionic liquid [J].

Bernini, Roberta ;

Mincione, Enrico ;

Barontini, Maurizio ;

Fabrizi, Giancarlo ;

Pasqualetti, Marcella ;

Tempesta, Sabrina .

TETRAHEDRON, 2006, 62 (33) :7733-7737

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