Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts
- Nikita S. AntonkinNikita S. AntonkinResearch School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Tomsk 634050, Russian FederationMore by Nikita S. Antonkin
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- Yulia A. VlasenkoYulia A. VlasenkoResearch School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Tomsk 634050, Russian FederationMore by Yulia A. Vlasenko
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- Akira YoshimuraAkira YoshimuraResearch School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Tomsk 634050, Russian FederationMore by Akira Yoshimura
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- Vladimir I. SmirnovVladimir I. SmirnovA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky Str., 1, Irkutsk 664033, Russian FederationMore by Vladimir I. Smirnov
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- Tatyana N. BorodinaTatyana N. BorodinaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky Str., 1, Irkutsk 664033, Russian FederationMore by Tatyana N. Borodina
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- Viktor V. ZhdankinViktor V. ZhdankinResearch School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Tomsk 634050, Russian FederationDepartment of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United StatesMore by Viktor V. Zhdankin
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- Mekhman S. Yusubov*Mekhman S. Yusubov*Email: [email protected] (M.S.Y.).Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Tomsk 634050, Russian FederationMore by Mekhman S. Yusubov
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- Alexandr Shafir*Alexandr Shafir*Email: [email protected] (A.S.).Department of Biological Chemistry, IQAC-CSIC, c/Jordi Girona 18-26, Barcelona 08034, SpainMore by Alexandr Shafir
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- Pavel S. Postnikov*Pavel S. Postnikov*Email: [email protected] (P.S.P.).Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, Tomsk 634050, Russian FederationDepartment of Solid-State Engineering, University of Chemistry and Technology, Prague 16628, Czech RepublicMore by Pavel S. Postnikov
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.
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