Microwave-assisted synthesis of indole- and azaindole-derivatives in water via cycloisomerization of 2-alkynylanilines and alkynylpyridinamines promoted by amines or catalytic amounts of neutral or basic salts

被引：52
作者：
Carpita, Adriano [2 ]
Ribecai, Arianna [1 ]
Stabile, Paolo [1 ]
机构：
[1] GlaxoSmithKline Med Res Ctr, Chem Dev Dept, I-37135 Verona, Italy
[2] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
来源：
TETRAHEDRON | 2010年 / 66卷 / 35期
关键词：
Microwaves; Indoles; Azaindoles; Cycloisomerization of alkynes; Water; Green chemistry; ONE-POT SYNTHESIS; NEAR-CRITICAL WATER; 2-ETHYNYLANILINE DERIVATIVES; ARYL IODIDES; INTRAMOLECULAR HYDROAMINATION; 2-SUBSTITUTED INDOLES; SONOGASHIRA REACTIONS; CYCLIZATION REACTIONS; CONVENIENT SYNTHESIS; EFFICIENT SYNTHESIS;
D O I：
10.1016/j.tet.2010.06.083
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient methodology is described and exploited for the preparation of differently substituted indoles and azaindoles via microwave-assisted cycloisomerization in water of 2-alkynylanilines and alkynylpyridinamines, which is promoted by catalytic amounts of neutral or basic salts or by stoichiometric weak organic bases. Good to high yields in the cyclization can be achieved for a variety of 2-amino (hetero)aryl alkynes. Reactions are run without any added metal catalyst. A comparison with the cycloisomerization conducted under conventional heating is also described. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7169 / 7178
页数：10
相关论文
共 94 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]  
BAZILE Y, 1977, EUR J MED CHEM, V12, P525
[8]  
BAZUREAU JP, 2006, MICROWAVES ORGANIC S, V1, P456
[9]  
BESSON T, 2005, MICROWAVE ASSISTED O, V74, P44
[10]  
BINET J, 2001, Patent No. 1919869
12345678910