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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Pyridine-to-Pyridazine Skeletal Editing.

Wonjun Choi1,2, Ahyoung Jang1,2, Sungwoo Hong1,2

  • 1Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, Korea.

Journal of the American Chemical Society
|October 31, 2025
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Summary
This summary is machine-generated.

Researchers developed a new method to convert pyridines into pyridazines, expanding access to these important pharmaceutical building blocks. This skeletal editing strategy offers a simple, scalable route to novel nitrogen-containing heterocycles.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Nitrogen-containing heterocycles are crucial in pharmaceuticals.
  • Pyridazines, with two adjacent ring nitrogens, are underexplored due to limited synthetic accessibility.
  • Pyridines are common pharmaceutical scaffolds, but their conversion to pyridazines is challenging.

Purpose of the Study:

  • To develop a novel skeletal editing strategy for converting pyridines into pyridazines.
  • To provide a simple, scalable, and broadly applicable method for accessing pyridazine scaffolds.
  • To expand heterocyclic chemical space for drug discovery and late-stage diversification.

Main Methods:

  • A two-step sequence involving N-amine assembly followed by m-chloroperoxybenzoic acid (mCPBA)-mediated ring remodeling.
  • The process facilitates carbon-to-nitrogen substitution, converting pyridine rings into pyridazines.
  • The reaction proceeds via a 1,2-diazatriene intermediate.

Main Results:

  • The method successfully converts pyridines to pyridazines while preserving aromaticity.
  • The process is operationally simple, runs at ambient temperature in air, and requires no specialized conditions or preinstalled groups.
  • Broad functional-group tolerance was observed, including with complex, drug-derived molecules.

Conclusions:

  • This skeletal editing strategy provides rapid and scalable access to pyridazines.
  • The developed method significantly expands the availability of pyridazine scaffolds for medicinal chemistry.
  • The platform enables late-stage diversification, facilitating drug discovery efforts.