Kohji Suda

Convenient syntheses of 2,4(5)-dialkylimidazoles and 1-methyl-2,4-dialkylimidazoles

Treatment of 2,4(5)-dialkyl-5(4)-phenylthioimidazoles with Raney nickel produced 2,4(5)-dialkylimidazoles. Methylation of 2,4(5)-dialkyl-5(4)-phenylthioimidazoles yielded 1-methyl-2,4-dialkylimidazoles, whereas methylation of 2,4(5)-dialkylimidazoles yielded in each case two isomers, the 1-methyl-2,4-dialkylimidazole and the 1-methyl-2,5-dialkylimidazole, which were not separated.

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

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.