Reactions of N-(1-cyanoalkyl)alkylideneamine N-oxides with dipolarophiles and nucleophiles. Part I. A novel synthesis of 2,4(5)-dialkyl-5(4)-phenylthioimidazoles

Abstract

Reactions of N-(1-cyanoalkyl)alkylideneamine N-oxides with thiols at room temperature yielded 2,4,5-trisub-stituted imidazoles (I). The reaction was accelerated by addition of a small amount of piperidine, and inhibited when carried out above the melting temperature of the nitrone in a solvent. The mechanism is discussed.