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Synthesis 2024; 56(01): 55-70
DOI: 10.1055/a-2013-9885
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
This 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).
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 reactionPublication History
Received: 19 December 2022
Accepted after revision: 16 January 2023
Accepted Manuscript online:
17 January 2023
Article published online:
16 February 2023
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