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Oxetane-to-azetidine skeletal editing.

Dayu Tian1, Like Luo1, Xian Xiao1

  • 1State Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, China.

Nature Chemistry
|July 13, 2026
PubMed
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Researchers developed a simple two-step method to convert oxetanes into azetidines using amines. This skeletal editing strategy offers a fast route to novel azetidine analogues for drug discovery.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Heterocyclic Chemistry

Background:

  • Heteroatom identity in bioactive molecules significantly impacts physicochemical and biological properties.
  • Exploring heterocycle analogues with diverse heteroatoms is crucial for identifying new therapeutic agents.
  • Traditional synthesis of these analogues often involves complex and time-consuming de novo methods.

Purpose of the Study:

  • To develop a straightforward and efficient method for synthesizing azetidines from readily available oxetanes.
  • To establish a versatile skeletal editing platform for rapid access to diverse azetidine derivatives.
  • To facilitate heterocycle modification in drug discovery programs.

Main Methods:

  • A two-step, one-pot strategy was employed for the direct skeletal transformation of oxetanes into azetidines.
  • The process involves Lewis acid-mediated intermolecular aminolysis of oxetanes with various amines.
  • Subsequent intramolecular Mitsunobu-type dehydrative cyclization forms the azetidine ring.

Main Results:

  • The developed method enables the direct conversion of oxetanes to azetidines under mild conditions.
  • The transformation demonstrates broad substrate scope, accommodating a wide range of aromatic and aliphatic amines.
  • The platform exhibits excellent functional group tolerance and compatibility with complex, drug-like molecules.

Conclusions:

  • This novel skeletal editing strategy provides rapid access to azetidine analogues from oxetane precursors.
  • The method simplifies the synthesis of valuable azetidine scaffolds for drug discovery.
  • It offers a powerful tool for heterocycle editing and the exploration of new chemical space in medicinal chemistry.