Facile synthesis of tetrahydroquinolines and julolidines through multicomponent reaction

被引:49
作者
Legros, Julien [1 ]
Crousse, Benoit [1 ]
Ourevitch, Michele [1 ]
Bonnet-Delpon, Daniele [1 ]
机构
[1] Fac Pharm Paris, CNRS, Lab BioCIS, F-92296 Chatenay Malabry, France
关键词
domino reaction; cycloaddition; fluorous alcohols; heterocycles; solvent effect;
D O I
10.1055/s-2006-947360
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldehydes, anilines and enol ethers react in trifluoroethanol (TFE) through an aza-Diels-Alder reaction (Povarov reaction) to afford the corresponding substituted tetrahydroquinolines. This reaction occurs, without any catalyst, under sequential three-component conditions, allowing thus the use of aliphatic aldehydes. In the presence of formaldehyde and an excess of dienophile, the product undergoes a second Povarov reaction affording new julolidine derivatives.
引用
收藏
页码:1899 / 1902
页数:4
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