A convenient approach to the synthesis of 2-(2-aminoethyl)pyrroles and their heterocyclization into hydrogenated pyrrolopyridines and related pyrroloindolizines
作者:Marina V Raiman、Aleksei V Pukin、Vladimir I Tyvorskii、Norbert De Kimpe、Oleg G Kulinkovich
DOI:10.1016/s0040-4020(03)00777-4
日期:2003.7
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
2-(2-氨基乙基)吡咯和2-(2-琥珀酰亚胺基乙基)吡咯由4-氧代链烷酸乙酯的乙缩醛通过潜在的乙烯基1,4-二羰基化合物作为关键中间体制备。2-(2-氨基乙基)吡咯与芳香族醛的Pictet-Spengler缩合反应以高收率得到4,5,6,7-四氢-1 H-吡咯并[3,2- c ]吡啶。从2-(2-琥珀酰亚胺基乙基)吡咯开始,以类似方式制备4,5,7,8,9,9a-六氢-3 H-吡咯并[2,3- g ]吲哚并酮。