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September 10, 2025Open Access

Skeletal editing of pyridines to aryldialdehydes

MYMeixin YanSichuan University YSYonglin ShiSichuan University CLCong LvSichuan University

Key Points

Pyridines can be transformed into aryldialdehydes, expanding synthetic options.
The method enables distinct electrophilic modification, unlike conventional nucleophilic approaches.
Utilizing the ANRORC process facilitates molecular diversification through new aromatic frameworks.
Conversion yields both arene-1,3-dialdehydes and naphthalene-1,3-dialdehydes, enhancing chemical utility.

Abstract

Electron-deficient nitrogen-containing aromatic heterocycles, particularly pyridine derivatives, can be converted into all-carbon aromatic frameworks via the ANRORC (Addition of Nucleophile, Ring-Opening, and Ring-Closing) skeletal editing process, providing a convenient tool for molecular diversification. However, reported methods are mainly limited to nucleophilic modification of ring-opening species. Herein, we report a distinct electrophilic modification method, smoothly converting pyridines into arene-1,3-dialdehydes or naphthalene-1,3-dialdehydes.

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