Oxadiazolone-Based Aromatic Annulations: A Nitrenoid Precursor for Tricyclic Aminoheterocycles

Nitrogen-containing heterocycles are present in most approved drugs, reflecting the significance of their synthetic strategies. By utilizing oxadiazolone as a nitrenoid (nitrene-like) precursor, we have developed a general strategy for the annulation with nucleophilic heterocycles to access various...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-11, Vol.89 (21), p.15542-15552
Main Authors: Zhu, W. Felix, Franz, Hanna M., Krämer, Andreas, Duman, Emre, Empel, Claire, Göbel, Michael W., Koenigs, Rene M., Knapp, Stefan, Hiesinger, Kerstin, Proschak, Ewgenij, Hernandez-Olmos, Victor
Format: Article
Language:English
Subjects:
Cyclization
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Oxadiazoles - chemistry
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Summary:Nitrogen-containing heterocycles are present in most approved drugs, reflecting the significance of their synthetic strategies. By utilizing oxadiazolone as a nitrenoid (nitrene-like) precursor, we have developed a general strategy for the annulation with nucleophilic heterocycles to access various polycyclic aminoheterocycles. We have discovered that 2-pyrryl-substituted substrates undergo a rearrangement, which indicates a spirocyclization–migration pathway. Given their fluorescence and biological activity as kinase hinge binders, these fragment-like aminoheterocycles represent potential starting points for applications in chemical biology and drug discovery.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01622