Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 15, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200274
Keywords
Fluorine; Heterocycles; Pyrazoles; Pyrimidines; Synthetic methods
Categories
Funding
- Enamine Ltd.
- Ministry of Education and Science of Ukraine [0121U100387 (21BF037-01M), 0122U001962 22BF037-02]
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Efficient approaches for the synthesis of fluorinated pyrazoles and pyrimidines with saturated (hetero)cyclic substituents were described. The methods rely on heterocyclizations using sp(3)-enriched beta-bromo-alpha,alpha-difluoroketones and fluorinated enaminones derived from saturated heterocyclic alpha-fluoroketones. These compounds serve as useful synthetic intermediates and meet the lead-oriented synthesis criteria.
Efficient approaches to the gram-scale synthesis of fluorinated pyrazoles and pyrimidines bearing saturated (hetero)cyclic substituents are described. The methods rely on the heterocyclizations of sp(3)-enriched beta-bromo-alpha,alpha-difluoroketones and fluorinated enaminones (in turn prepared from saturated heterocyclic alpha-fluoroketones), respectively; these compounds themselves are useful synthetic intermediates that have been prepared on multigram scale for the first time. LogP and aqueous solubility measurements, as well as lead-likeness assessment using the Nelson's LLAMA tool show that the 19 synthesized sp(3)-enriched fluorinated building blocks meet the lead-oriented synthesis criteria.
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