Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole N-oxides, and aldehydes
Ekaterina S Uvarova1, Anton V Kutasevich1, Egor S Lipatov2,3
1Mendeleev University of Chemical Technology, Miusskaya Sq., 9, Moscow 125047, Russian Federation. mityanovvs@yandex.ru.
Abstract:
A three-component condensation of 2-unsubstituted imidazole N-oxides, 3-ketonitriles, and aldehydes is described. The reaction proceeds via sequential Knoevenagel condensation/Michael addition under mild, catalyst-free conditions with various substrates. Furthermore, the corresponding 2-functionalized imidazole N-oxides can be further dehydrated to (Z)-2-aroyl-3-(1H-imidazol-2-yl)-acrylonitriles, which may also be directly prepared by changing the reaction conditions as a cascade of Knoevenagel condensation/Michael addition/dehydration.
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