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August 20, 2025Open Access

Oxazinoazaarenes as Versatile Intermediates for Regioselective Late-Stage C–H-Functionalization and Skeletal Editing of Pyridines, Isoquinolines and Quinolines

Key Points

Oxazinoazaarenes facilitate regioselective C–H functionalization, allowing targeted modifications in azaarenes.
Recent methods show significant innovation in modifying pyridines, especially through para- and meta-C–H bond strategies.
The approach utilizes late-stage skeletal editing for enhancing structure–activity relationship evaluations across various applications.
Innovative modifications through oxazinoazaarenes may support the development of new functional materials and pharmaceuticals.

Abstract

Azaarenes, particularly pyridines, represent some of the most important structural and functional motifs across various fields. Consequently, late-stage C–H bond functionalization and skeletal editing of azaarenes hold significant value, particularly for accelerating structure–activity relationship studies. Dearomatized intermediates derived from such azaarenes offer an innovative strategy for selectively modifying these valuable cores. Among them, oxazinoazaarenes are a practical and scalable platform for regioselective meta- and para-C–H functionalization and skeletal editing of the azaarene moiety. This short review highlights the advancements in oxazinoazaarene-based pyridine modification methods achieved by our group and others.

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