Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts
Nikita S. Antonkin, Yulia А. Vlasenko, Akira Yoshimura, Владимир И. Смирнов, Tatyana N. Borodina, Viktor V. Zhdankin, Mekhman S. Yusubov, Alexandr Shafir, Павел С. Постников
Abstract
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.