Multicomponent synthesis of 2-imidazolines

RS Bon, B. van Vliet, N.E. Sprenkels, R.F. Schmitz, FJJ de Kanter, C.V. Stevens, M Swart, FM Bickelhaupt, MB Groen, RVA Orru

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Abstract

A multicomponent reaction (MCR) between amines, aldehydes, and isocyanides bearing an acidic α-proton gives easy access to a diverse range of highly substituted 2-imidazolines. The limitations of the methodology seem to be determined by the reactivity of the isocyanide and by the steric bulk on the in situ generated imine rather than by the presence of additional functional groups on the imine. Less reactive isocyanides, for example p-nitrobenzyl isocyanide 25a, react successfully with amines and aldehydes, using a catalytic amount of silver(I) acetate. Some of the resulting p-nitrophenyl-substituted 2-imidazolines undergo air oxidation to the corresponding imidazoles. Differences in reactivity of the employed isocyanides are explained with use of DFT calculations. Difficult reactions with ketones instead of aldehydes as the oxo-compound in this MCR are promoted by silver(I) acetate as well.
Original languageEnglish
Pages (from-to)3542-3553
Number of pages11
JournalJournal of Organic Chemistry
Volume70
Issue number9
Early online date30 Mar 2005
DOIs
Publication statusPublished - 1 Apr 2005

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