Issue 21, 2024

Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole N-oxides, and aldehydes

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.

Graphical abstract: Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole N-oxides, and aldehydes

Supplementary files

Article information

Article type
Paper
Submitted
04 Mar 2024
Accepted
01 May 2024
First published
02 May 2024

Org. Biomol. Chem., 2024,22, 4297-4308

Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole N-oxides, and aldehydes

E. S. Uvarova, A. V. Kutasevich, E. S. Lipatov, I. S. Pytskii, O. A. Raitman, Y. M. Selivantev and V. S. Mityanov, Org. Biomol. Chem., 2024, 22, 4297 DOI: 10.1039/D4OB00353E

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