Unusual methylene transfer in reactions of Simmons–Smith reagent with 1,3-diazabuta-1,3-dienes: synthesis of functionalised imidazole derivatives

The reactions of Simmons–Smith reagent with 1-aryl-2-phenyl-4-methylthio-4-secondary amino 1,3-diazabuta-1,3-dienes underwent an unusual 1,4-methylene transfer resulting in the formation of 1-aryl-2-phenyl-4-secondary amino imidazoles . Whereas, its reactions with 1-aryl-2-phenyl-4-secondary amino-1,3-diazabuta-1,3-dienes underwent an initial 1,2-methylene transfer leading to an aziridine intermediate which rearranges to 1-aryl-4-phenyl-imidazoles .