Versatile base-catalyzed route to polycyclic heteroaromatic compounds by intramolecular Aza-Michael addition

被引：27

作者：

Bandini, Marco ^{[1
]}

Eichholzer, Astrid ^{[1
]}

Monari, Magda ^{[1
]}

Piccinelli, Fabio ^{[1
]}

Umani-Ronchi, Achille ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 18期

关键词：

catalysis; indole; Michael addition; natural compounds; pyrrole;

D O I：

10.1002/ejoe.200601139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic new synthetic approach to 3,4-dihydropyrazino[ 1,2-a]indol-1 (2H) -ones by intramolecular 1,4-dddition of readily available alpha,beta-unsaturated esters, is described. Here, the use of a range of organic as well as inorganic bases (5-10 mol-%) allowed a fast (30 min) and regioselective ring-closing reaction to be performed in high yields under simpleoperational conditions. Moreover, the protocol was effectively employed, as the key step, in the synthesis of the dibromopyrrolo alkaloid derivative N-Bn-longamide b. ((c) Wiley-VCH Verlag GmbH & Co.

引用

页码：2917 / 2920

页数：4