Recent Advances in the Dearomative Skeletal Editing of Mono-azaarenes

Pengke Zhang; Lin Hua; Tamotsu Takahashi; Shengnan Jin; Qilin Wang

doi:10.1055/a-2013-9885

Synthesis, Table of Contents

Synthesis 2024; 56(01): 55-70
DOI: 10.1055/a-2013-9885

special topic

Advances in Skeletal Editing and Rearrangement Reactions

Recent Advances in the Dearomative Skeletal Editing of Mono-azaarenes

Pengke Zhang

^bInstitute of Chemistry Co. Ltd, Henan Academy of Sciences, Zhengzhou 450002, P. R. of China

,

Lin Hua

^bInstitute of Chemistry Co. Ltd, Henan Academy of Sciences, Zhengzhou 450002, P. R. of China

,

Tamotsu Takahashi

^bInstitute of Chemistry Co. Ltd, Henan Academy of Sciences, Zhengzhou 450002, P. R. of China

,

Shengnan Jin∗

^aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. of China

,

Qilin Wang ∗

^aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

Despite its challenges, the skeletal editing of mono-azaarenes (pyridines, quinolines, and isoquinolines) has shown unparalleled synthetic utility in the construction of complex molecules that are difficult to access by conventional methods. In this short review, we summarize the three most recently developed skeletal editing strategies for the deconstruction of azaarene cores, with a focus on their generality, limitations, and mechanistic aspects. Also, the application of the skeletal editing strategy in the total synthesis of some important natural products is discussed.

1 Introduction

2 Skeletal Editing of Mono-Azaarenes through Zincke-like Reactions

3 Skeletal Editing of Mono-azaarenes through Aza-Buchner Reactions

4 Skeletal Editing of Mono-azaarenes via Photoinduced Radical or Energy-Transfer Processes

5 Conclusion

Key words

mono-azaarene - dearomatization - skeletal editing - functionalization - Zincke reaction - Buchner reaction - photoinduced reaction

Full Text

References

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