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Comptes Rendus Chimie
Volume 5, n° 3
pages 171-175 (mars 2002)
Received : 26 June 2000 ;  accepted : 6 February 2002
Conditions de la condensation de Knoevenagel-Cope pour la synthèse de cétones ,β-éthyléniques
Knoevenagel-Cope condensation conditions applied to ketolisation reaction.

Michel  Guerro a ,  Albert  Robert a * ,  Gwendal  Michelot b ,  Nicolas  Valentic b
aLaboratoire SESO, UMR 6510, université Rennes-1, bât. 10A, campus de Beaulieu, 35042 Rennes, France 
bValchim S.A., 2, rue Fernand-Forest, Zone industrielle, 78520 Limay, France 

*Correspondance et tirés à part

La condensation de Knoevenagel-Cope entre l'acétophénone et le cyanoacétate d'éthyle conduit majoritairement au 2-cyano-3-phényl-but-2-énoate d'éthyle et à une dihydropyridone substituée. La recherche de l'origine de ce produit secondaire cyclique montre qu'il provient d'une cétolisation de l'acétophénone. Cette étude nous a conduit à décrire une nouvelle voie d'accès à des cétones α,β-insaturatées, en utilisant simplement les conditions de la réaction de Knoevenagel-Cope.

Mots clés  : Knoevenagel-Cope ; cétones α,β-insaturatées ; dihydropyridones substituées.


The Knoevenagel-Cope condensation between acetophenone and ethyl cyanoacetate mainly gives 2-cyano-3-phenyl-but-2-enoic acid ethyl ester and a substituted dihydropyridone as a secondary product. We show that this secondary product arises from a ketolisation reaction of acetophenone. As a consequence, we describe a new convenient way to prepare some α,β-insaturated ketones by using the Knoevenagel-Cope reaction conditions.

Mots clés  : Knoevenagel-Cope ; α,β-insaturated ketones ; substituted dihydropyridones.

© 2002  Académie des sciences / Éditions scientifiques et médicales Elsevier SAS. All Rights Reserved.

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