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Synthesis 2024; 56(24): 3793-3814
DOI: 10.1055/a-2395-5804
DOI: 10.1055/a-2395-5804
review
Skeletal Editing through Single-Atom Insertion and Transmutation: An Insight into a New Era of Synthetic Organic Chemistry
C.C.M. thanks the Science and Engineering Research Board (SERB), New Delhi, for research grants (CRG/2020/004509 and ECR/2016/000337) and the National Institute of Technology (NIT) Manipur for financial support. C.K.P and K.K. are grateful to the Ministry of Education (MoE), New Delhi, India for fellowship support.
Abstract
Considering the importance of heterocycles, significantly represented in medicinal chemistry and drug development, the single-atom insertion technique and transmutation strategy provide productive approaches towards complicated molecular structures through heterocycle diversification. It shows a potentially powerful approach for modifying complex substrates concisely and chemospecifically. Although skeletal editing applies to cyclic and acyclic compounds, this review focuses on the diversification of carbo- and heterocyclic compounds for synthesizing various medicinally important molecules via the single-atom insertion technique. The classification system is based on recent and critical historical methods of single-atom insertion as applied to the transmutation of aromatic rings.
1 Introduction
2 Skeletal Editing through Carbon-Atom Insertion
2.1 Skeletal Editing of Indoles and Pyrroles Derivatives: Carbon-Atom Insertion into a C=C Bond
2.2 Skeletal Editing of Pyrazole and Indazole Derivatives: Carbon-Atom Insertion into an N–N Bond
2.3 Skeletal Editing of Pyrazole and Indazole Derivatives: Insertion of CF3 Group into Heteroarenes
2.4 Skeletal Editing of Imidazole Derivatives: Carbon-Atom Insertion into C–N Bond
2.5 Skeletal Editing through Atom-to-Atom Transmutation
3 Skeletal Editing through N-Atom Insertion
3.1 Nitrogen-Atom Insertion into Carbocycles
3.2 Nitrogen-Atom Insertion into Heterocycles
3.3 Carbon to Nitrogen Transmutation
3.3 Molecular Editing through Isotopic Transmutation
4 Conclusion
Key words
atom insertion - atom exchange - skeletal editing - molecular editing - heterocycle diversificationPublication History
Received: 12 June 2024
Accepted after revision: 20 August 2024
Accepted Manuscript online:
20 August 2024
Article published online:
25 September 2024
© 2024. Thieme. All rights reserved
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