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Iminoalkylation Des Ènamines Avec Des Nitriles Via Le Sel De Nitrilium: Une Nouvelle Méthode De Synthèse D'Ènaminocétones Et De β‐Dicétones.

par Baudoux, Dominique ;Fuks, Robert
Référence Bulletin des Sociétés chimiques belges, 93, 11, page (1009-1018)
Publication Publié, 1984

Article révisé par les pairs

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Résumé :

The reaction of nitrilium salts with enamines leads to a mixture of enaminimines 4 and enaminoketones 5 by an iminoalkylation reaction. Partial hydrolysis of 4 with diluted acetic acid leads to the isolation of these new enaminoketones 5 in high yields. Refluxing them in HCl 6 N give β‐diketones, well described and usually obtained by acylation of enamines with acid chlorides. The nitrilium salt being easily prepared “in situ” from the corresponding nitrile this reaction constitutes a novel way to enaminoketones 5 and β‐diketones 6. A nitrilium salt being a much stronger electrophile than an acid chloride, the experimental conditions are milder and do not need the presence of triethylamine. The scope and limits of this novel reaction in relation to the nature of the starting nitrile are discussed. Copyright © 1984 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim