Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts

Nikita S. Antonkin, Yulia A. Vlasenko, Akira Yoshimura, Vladimir I. Smirnov, Tatyana N. Borodina, Viktor V. Zhdankin, Mekhman S. Yusubov, Alexandr Shafir, Pavel S. Postnikov

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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.

Original languageEnglish (US)
Pages (from-to)7163-7178
Number of pages16
JournalJournal of Organic Chemistry
Issue number10
StatePublished - May 21 2021

Bibliographical note

Funding Information:
The heterocyclization study was supported by the Russian Science Foundation (project No. 17-73-20066). Y.A.V. kindly acknowledges the financial support from the Russian Foundation of Basic Research for the development of oxidative cyclization process (project No. 20-33-90007). This work was funded by Spain’s MINECO (CTQ2017-86936-P), AGAUR (2017 SGR 01051), and additional support from CSIC. The authors would like to acknowledge the Multi-Access Chemical Research Center SB RAS (N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry) and the Center for Chemical Analysis and Materials Research of Saint Petersburg State University for analytical measurements. X-ray structural results were obtained using the material and technical base of the Baikal Analytical Center for Collective Use of the SB RAS.

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