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Updated: May 16, 2025
11:45
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
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Alkyl Azetidines Via Batch and Flow Photochemistry
Oleksandr P Datsenko1, Andrii Baziievskyi1, Iryna Sadkova1
1Enamine Ltd, Winston Churchill St. 78, 02094 Kyiv, Ukraine.
Organic Letters
|April 4, 2025
Summary
Photochemical modifications of azetidine-2-carboxylic acids yield valuable alkyl azetidines. This method is scalable for drug discovery applications, demonstrated in batch and flow processes.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Photochemistry
Background:
- Azetidine-2-carboxylic acids are versatile scaffolds.
- Efficient synthesis of functionalized azetidines is crucial for drug discovery.
- Photochemical reactions offer unique synthetic pathways.
Purpose of the Study:
- To develop a photochemical method for synthesizing alkyl azetidines.
- To demonstrate the scalability of the reaction in both batch and flow conditions.
- To provide novel building blocks for pharmaceutical research.
Main Methods:
- Photochemical modification of azetidine-2-carboxylic acids.
- Utilizing both batch and continuous flow reactor setups.
- Purification and characterization of the synthesized alkyl azetidines.
Main Results:
- Successful preparation of various alkyl azetidines.
- Demonstration of reaction scalability from milligram to multigram quantities.
- High yields and purity of the target compounds were achieved.
Conclusions:
- Photochemical synthesis is an effective route to alkyl azetidines.
- The developed method is robust and scalable for practical applications.
- The synthesized azetidines serve as valuable intermediates in drug discovery programs.
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