REACTION OF ELECTRON-RICH ALKENES WITH ANILINES AND FORMALDEHYDE - SYNTHESES OF TETRAHYDROQUINOLINES

被引：63

作者：

MELLOR, JM

MERRIMAN, GD

机构：

[1] Department of Chemistry, Southampton University, Southampton

来源：

TETRAHEDRON | 1995年 / 51卷 / 21期

关键词：

D O I：

10.1016/0040-4020(95)00269-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot synthesis has been established of tetrahydroquinolines based upon reaction of aromatic amines and formaldehyde with electron rich alkenes such as styrene, alpha-methylstyrene, 1-phenylcyclohexene and 3,4-dihydro-2H-pyran. The isolation of alcohols as additional products from reactions conducted in acetonitrile containing trifluoroacetic acid, and the demonstration that these alcohols reacted further under similar reaction conditions to give efficiently cyclised products indicates that the cyclisations reported in this paper are not concerted. The importance is discussed of similar multi-step processes in the catalysed addition of electron rich alkenes to preformed imines.

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页码：6115 / 6132

页数：18

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