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DOI: 10.1055/s-0043-1775110
Heterocyclic Surgery for Isotopic Labeling
The author (JMS) is grateful to Florida State University (FSU), the National Science Foundation, Division of Chemistry (CHE-2154226), and the National Institutes of Health, National Institute of General Medical Sciences (R35GM150795) for funding.
This manuscript is dedicated to the memory of Zachary A. Tolchin
Abstract
Recent developments in the isotopic labeling of heteroarenes may prove to be useful in the realms of biomedical science, materials chemistry, and fundamental organic chemistry. The use of the age-old Zincke reaction, or tactical variants thereof, has become particularly utilitarian in effecting single-atom nitrogen replacement in various azines to generate their desired isotopologues. This chemistry can be synthetically leveraged at an early stage for diversity-oriented heterocyclic labeling of pharmaceuticals and/or natural products. Additionally, given the prevalence of saturated azacycles in biologically relevant molecules, access to these isotopologues becomes relevant through dearomative retrosynthetic analysis from the corresponding 15N-labeled heteroarenes.
1 Introduction
2 Our Lab’s Development of the 15NRORC Reaction
3 Other Recent Azine-Labeling Methods
4 Expanded ANRORC Utilization
5 Conclusion and Outlook
Publication History
Received: 21 May 2024
Accepted after revision: 28 August 2024
Article published online:
26 September 2024
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