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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
b   Institute of Chemistry Co. Ltd, Henan Academy of Sciences, Zhengzhou 450002, P. R. of China
,
Lin Hua
b   Institute of Chemistry Co. Ltd, Henan Academy of Sciences, Zhengzhou 450002, P. R. of China
,
Tamotsu Takahashi
b   Institute of Chemistry Co. Ltd, Henan Academy of Sciences, Zhengzhou 450002, P. R. of China
,
Shengnan Jin∗
a   College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. of China
,
Qilin Wang  ∗
a   College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (22101073 and U1504206), the Key Teacher Project of Henan Province of China (2021GGJS025), China Postdoctoral Science Foundation (2020M672200), and Henan University (SYL20060149).
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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


Publication History

Received: 19 December 2022

Accepted after revision: 16 January 2023

Accepted Manuscript online:
17 January 2023

Article published online:
16 February 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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