One-step synthesis of N-[(methylthio)methyl]imidazole and related heterocyclic derivatives via a fummerer rearrangement

N-(Methylthio)methyl]imidazole may be prepared from dimethylsulfoxide and N-(trimethylsilyl)imidazole or N-(t-butyldimethylsilyl)imidazole at elevated temperatures via a Purnmerer rearrangement. The product was characterized by elemental analysis, mass spectrometry and proton and carbon nmr. Preliminary experiments show that corresponding derivatives of 2-methylimidazole, pyrazole, triazole and benzimidazole may also be prepared in an analogous manner.