Synthesis of 7H-indolo[2,3-c]quinolines:: Study of the Pd-catalyzed intramolecular arylation of 3-(2-bromophenylamino)quinolines under microwave irradiation

被引：60

作者：

Hostyn, S ^{[1
]}

Maes, BUW ^{[1
]}

Van Baelen, G ^{[1
]}

Gulevskaya, A ^{[1
]}

Meyers, C ^{[1
]}

Smits, K ^{[1
]}

机构：

[1] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

来源：

TETRAHEDRON | 2006年 / 62卷 / 19期

关键词：

palladium; amination; Heck-type reaction; microwave; Malaria;

D O I：

10.1016/j.tet.2005.12.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

D-ring substituted 5-methyl-5H-indolo[2,3-c]quinolines (4) have been synthesized in three steps starting from commercially available 3-bromoquinoline (5) and 2-bromoanilines (6). The methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald-Hartwig amination followed by a regioselective intramolecular Heck-type reaction. The latter step has been investigated under microwave irradiation. Heating at 180 degrees C allows to seriously reduce the catalyst loading and get a full conversion to reaction product in 10 min. In addition, the former simplifies the purification. (c) 2006 Elsevier Ltd. All rights reserved.

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页码：4676 / 4684

页数：9

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