Synlett 2006(12): 1899-1902  
DOI: 10.1055/s-2006-947360
LETTER
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Tetrahydroquinolines and Julolidines through ­Multicomponent Reaction

Julien Legros*, Benoit Crousse*, Michèle Ourévitch, Danièle Bonnet-Delpon
Laboratoire BioCIS-CNRS, Faculté de Pharmacie-Paris Sud, rue J. B. Clément, 92296 Châtenay-Malabry, France
Fax: +33(1)46835740; e-Mail: benoit.crousse@cep.u-psud.fr; e-Mail: julien.legros@cep.u-psud.fr;
Further Information

Publication History

Received 18 May 2006
Publication Date:
24 July 2006 (online)

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Abstract

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.