Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts

A novel approach to the preparation of imidazole-substituted cyclic iodonium salts has been developed via the oxidative cyclization of 1-phenyl-5-iodoimidazole using a cheap and available Oxone/H2SO4 oxidative system. The structure of the new polycyclic heteroarenes has been confirmed by single-crystal X-ray diffractometry, revealing the characteristic structure features for cyclic iodonium salts. The newly produced imidazole-flanked cyclic iodonium compounds were found to readily engage in a heterocyclization reaction with elemental sulfur, affording benzo[5,1-b]imidazothiazoles in good yields.

Automated summary

A novel method has been developed for the synthesis of imidazole-substituted cyclic iodonium salts via oxidative cyclization reaction of 1-phenyl-5-iodoimidazole. The newly synthesized compounds can readily react with elemental sulfur to afford benzo[5,1-b]imidazothiazoles in good yields. Single-crystal X-ray diffractometry confirmed the structure of the new polycyclic heteroarenes, revealing the characteristic features for cyclic iodonium salts.