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Molecular editing

Converting benzene to pyridine

Nature Reviews Chemistry volume 7, page 71 (2023)Cite this article

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Functional-group interconversion is a fundamental technique for chemists to construct new molecules and expand the accessible chemical space. However, such transformations are usually restricted to changing specific substituents on the periphery of a molecular scaffold, with only a limited number of examples enabling the modification of a molecule’s backbone architecture. Among them, converting a carbocyclic arene to its nitrogen-containing heterocyclic analogue by swapping a single carbon for a nitrogen is highly sought-after, owing to the prevalence of nitrogen-containing heterocycles in biologically active compounds. Such a unique transformation, that might look like a typographical error on paper, allows the direct access to pyridine analogues without having to resort to de novo synthesis.

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References

Original article

  • Patel, S. C. & Burns, N. Z. Conversion of aryl azides to aminopyridines. J. Am. Chem. Soc. 144, 17797–17802 (2022)

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Related article

  • Sundberg, R. J., Suter, S. R. & Brenner, M. Photolysis of ortho-substituted aryl azides in diethylamine. Formation and autoxidation of 2-diethylamino-1 H-azepine intermediates. J. Am. Chem. Soc. 94, 513–520 (1972)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Medicinal Chemistry, Research and Early Development, Cardiovascular, Renal and Metabolism (CVRM), BioPharmaceuticals R&D, AstraZeneca, Gothenburg, Sweden

    Elisa Y. Lai & Lucas Guillemard

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  1. Elisa Y. Lai
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  2. Lucas Guillemard
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Correspondence to Elisa Y. Lai or Lucas Guillemard.

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Lai, E.Y., Guillemard, L. Converting benzene to pyridine. Nat Rev Chem 7, 71 (2023). https://doi.org/10.1038/s41570-023-00465-2

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  • DOI: https://doi.org/10.1038/s41570-023-00465-2

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