Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases

被引:24
作者
Carpita, Adriano [2 ]
Ribecai, Arianna [1 ]
机构
[1] GlaxoSmithKline SpA, Chem Dev Dept, I-37135 Verona, Italy
[2] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
关键词
Indoles; Water; Cycloisomerization; Microwaves; 2-Alkynylanilines; Green chemistry; ONE-POT SYNTHESIS; NEAR-CRITICAL WATER; 2-ETHYNYLANILINE DERIVATIVES; INTRAMOLECULAR HYDROAMINATION; 2-SUBSTITUTED INDOLES; CYCLIZATION REACTIONS; CONVENIENT SYNTHESIS; TERMINAL ALKYNES; ARYL IODIDES; PALLADIUM;
D O I
10.1016/j.tetlet.2009.09.135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented green methodology is described for the preparation of differently substituted indoles via microwave-assisted cycloisomerization of 2-alkynylaniline derivatives in water. Moderate to good yields in the cyclization can be achieved for a variety of 2-aminoaryl alkynes. Reactions are run without any added metal catalyst, acid, or base, and do not take place by applying conventional heating. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6877 / 6881
页数:5
相关论文
共 72 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]   2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates [J].
Ambrogio, Ilaria ;
Cacchi, Sandro ;
Fabrizi, Giancarlo .
TETRAHEDRON LETTERS, 2007, 48 (43) :7721-7725
[3]   Gold-catalyzed synthesis of 2-substituted, 2,3-Disubstituted and 1,2,3-trisubstituted Indoles in [bmim]BF4 [J].
Ambrogio, Ilaria ;
Arcadi, Antonio ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Marinelli, Fabio .
SYNLETT, 2007, (11) :1775-1779
[4]  
Arcadi A, 2004, HETEROCYCLES, V64, P475
[5]   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
[6]  
Arcadi A., 2004, SYNTH, V4, P610
[7]   Electrochemical-mediated cyclization of 2-alkynylanilines: A clean and safe synthesis of indole derivatives [J].
Arcadi, Antonio ;
Bianchi, Gabriele ;
Inesi, Achille ;
Marinelli, Fabio ;
Rossi, Leucio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (05) :783-787
[8]  
BAZUREAU JP, 2006, MICROWAVES ORGANIC S, V1, P456
[9]  
BESSON T, 2005, MICROWAVE ASSISTED O, V74, P44
[10]  
BINET J, 2007, Patent No. 20058858