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Synthesis of Imidazoles and Oxazoles by Aldimine Cross-Coupling
C. Kison, T. Opatz*
Johannes Gutenberg-Universität Mainz and Universität Hamburg, Germany
23 March 2009 (online)
Reported here are the syntheses of tetrasubstituted imidazoles and trisubstituted oxazoles in one or two steps from α-acylamino-imines 5 which are readily obtained by 1,2-addition of N-monosubstituted α-aminonitriles 1 to N-acylimines 2. The intermediates 3 are subjected to the next DBU-catalyzed step without purification to give imidazoles 4 and intermediates 5; the cyclization directly to 4 is promoted by bulky substituents in the 5-position. The intermediates 5 are converted into oxazoles 6 in simple steps and purification is then achieved by column chromatography.