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.

A E Favorsky Irkutsk Institute of Chemistry Siberian Branch of the Russian Academy of Sciences Favorsky Str 1 Irkutsk 664033 Russian Federation

Department of Biological Chemistry IQAC CSIC c Jordi Girona 18 26 Barcelona 08034 Spain

Department of Chemistry and Biochemistry University of Minnesota Duluth Duluth Minnesota 55812 United States

Department of Solid State Engineering University of Chemistry and Technology Prague 16628 Czech Republic

Research School of Chemistry and Applied Biomedical Sciences Tomsk Polytechnic University Tomsk 634050 Russian Federation

Citace poskytuje Crossref.org

Zwitterionic iodonium species afford halogen bond-based porous organic frameworks