Synthesis 2020; 52(16): 2299-2310
DOI: 10.1055/s-0040-1707122
short review
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

a  Department of Chemistry and Biochemistry, University of Minnesota Duluth, Minnesota 55812, USA   Email: ayoshimu@d.umn.edu   Email: vzhdanki@d.umn.edu
,
Akio Saito
b  Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-23-16 Naka-cho, Koganei, Tokyo 184-8588, Japan   Email: akio-sai@cc.tuat.ac.jp
,
c  Research School of Chemistry and Applied Biomedical Sciences, The Tomsk Polytechnic University, 634050 Tomsk, Russian Federation
,
a  Department of Chemistry and Biochemistry, University of Minnesota Duluth, Minnesota 55812, USA   Email: ayoshimu@d.umn.edu   Email: vzhdanki@d.umn.edu
› Author Affiliations
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).
Further Information

Publication History

Received: 08 March 2020

Accepted after revision: 15 April 2020

Publication Date:
18 May 2020 (online)


Akira Yoshimura and Akio Saito contributed equally to this work.

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

 
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