Efficient base-catalyzed 5-exo-dig cyclization of carbonyl groups on unactivated alkynyl-quinolines:: An entry to versatile oxygenated heterocycles related to the furoquinoline alkaloids family

被引：35

作者：

Godet, T ^{[1
]}

Bosson, J ^{[1
]}

Belmont, P ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5181, F-69622 Villeurbanne, France

来源：

SYNLETT | 2005年 / 18期

关键词：

quinoline; 5-exo-dig cyclization; 1,3-dihydrofuro[3,4-b]quinoline; base-catalyzed cyclization;

D O I：

10.1005/s-2005-918953

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient 5-exo-dig cyclization was observed when TMS-protected alkynyl-quinolines bearing a carbonyl group were submitted to a mixture of an alcohol (alkyl-OH, diol, amino alcohol) with an inorganic base (K2CO3). The cyclization process seems to go through the deprotection of the TMS group prior to the cyclization step. The dihydrofuroquinoline derivatives formed are structurally related to the well-known furoquinoline alkaloids family. The scope and limitations of this reaction have also been studied with diverse bases and various alkynyl and carbonyl derivatives.

引用

页码：2786 / 2790

页数：5

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