Synthesis of oxazoline and oxazole derivatives by hypervalent-iodine-mediated oxidative cycloaddition reactions

Akira Yoshimura, Akio Saito, Mekhman S. Yusubov, Viktor V. Zhdankin

Research output: Contribution to journalReview articlepeer-review

4 Scopus citations

Abstract

Organohypervalent iodine reagents are widely used for the preparation of various oxazolines, oxazoles, isoxazolines, and isoxazoles. In the formation of these heterocyclic compounds, hypervalent iodine species can serve as the activating reagents for various substrates, as well as the heteroatom donor reagents. In recent research, both chemical and electrochemical approaches toward generation of hypervalent iodine species have been utilized. The in situ generated active species can react with appropriate substrates to give the corresponding heterocyclic products. In this short review, we summarize the hypervalent-iodine-mediated preparation of oxazolines, oxazoles, isoxazolines, and isoxazoles starting from various substrates. 1 Introduction 2 Synthesis of Oxazolines 3 Synthesis of Oxazoles 4 Synthesis of Isoxazolines 5 Synthesis of Isoxazoles 6 Conclusion.

Original languageEnglish (US)
Article numberss-2020-m0131-sr
Pages (from-to)2299-2310
Number of pages12
JournalSynthesis (Germany)
Volume52
Issue number16
DOIs
StatePublished - Aug 18 2020
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081-P), the Tomsk Polytechnic University Competitiveness Enhancement Program and the National Science Foundation (CHE-1759798). A.S. is grateful to the Japan Society for the Promotion of Science (JSPS), Fund for the Promotion of Joint International Research (Grant No. 16KK0199).RussianScienceFoundation(RSF-16-13-10081-P)TomskPolytechnicUniversityCompetitivenessEnhancementProgram()NationalScienceFoundation(CHE-1759798)JapanSocietyforthePromotionofScience(16KK0199)

Publisher Copyright:
© 2020 American Institute of Physics Inc.. All rights reserved.

Keywords

  • hypervalent iodine
  • isoxazoles
  • isoxazolines
  • oxazoles
  • oxazolines
  • oxidative cyclization
  • oxidative cyclo-addition

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