A convenient approach to the synthesis of 2-(2-aminoethyl)pyrroles and their heterocyclization into hydrogenated pyrrolopyridines and related pyrroloindolizines

被引：17

作者：

Raiman, MV

Pukin, AV

Tyvorskii, VI

De Kimpe, N

Kulinkovich, OG

机构：

[1] Belarusian State Univ, Dept Organ Chem, Minsk 220050, BELARUS

[2] Univ Ghent, Fac Agr & Appl Biol Sci, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

TETRAHEDRON | 2003年 / 59卷 / 28期

关键词：

cyclopropanols; 2-aminoethylpyrroles; pyrrolopyridines; pyrroloindolizines; Pictet-Spengler reaction;

D O I：

10.1016/S0040-4020(03)00777-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(2-Aminoethyl)pyrroles and 2-(2-succinimidoethyl)pyrroles were prepared from acetals of ethyl 4-oxoalkanoates via latent vinyl 1,4-dicarbonyl compounds as the key intermediates. The Pictet-Spengler condensation of 2-(2-aminoethyl)pyrroles with aromatic aldehydes gave 4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines in good yields. 4,5,7,8,9,9a-Hexahydro-3H-pyrrolo[2,3-g]indolizines were prepared in a similar way starting from 2-(2-succinimidoethyl)pyrroles. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：5265 / 5272

页数：8

共 20 条

[11] Indolizidine and quinolizidine alkaloids [J].