Formal pyridine meta-azidation and its application for the synthesis of diazepines, ring-fused δ-carbolines and 1,2,3-triazolylpyridines

Shu-Min Guo, Pengwei Xu, Constantin G. Daniliuc and Armido Studer ()
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Shu-Min Guo: Universität Münster
Pengwei Xu: Universität Münster
Constantin G. Daniliuc: Universität Münster
Armido Studer: Universität Münster

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract The nitrogen atom serves as an important structural element in pharmacologic studies, highlighting the critical role of nitrogen-containing heterocycles in drug discovery. Late-stage peripheral functionalization and structural editing of nitrogen-containing heterocycles have garnered increasing attention due to their potential for the preparation of diversifying drug-like libraries. In particular, the structural diversification of pyridine cores by introducing N atoms or N-containing functionalities shows promise, but remains underexplored. Here, we report a synthetic strategy that combines the introduction of the versatile azide moiety with molecular editing. This approach comprises an initial peripheral regioselective meta-azidation of pyridines through dearomatized oxazino pyridine intermediates, and a subsequent molecular editing step via a photo-mediated singlet nitrene insertion process. We have demonstrated the utility of this strategy by the synthesis of seven-membered diazepines. Furthermore, ring-fused δ-carbolines and 1,2,3-triazolylpyridines can be also accessed through chemical manipulation of the azide functionality.

Date: 2025
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DOI: 10.1038/s41467-025-65313-x

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