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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)7163-7178
Number of pages16
JournalJournal of Organic Chemistry
Volume86
Issue number10
DOIs
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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PubMed: MeSH publication types

  • Journal Article
  • Research Support, Non-U.S. Gov't

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