Ring-opening difluorination of pyrazoloazines

We have developed a novel ring-opening difluorination process for pyrazoloazines. Utilizing 2.5 equivalents of Selectfluor®, this method enables electrophilic difluorination and subsequent ring-opening of pyrazoloazines, yielding the corresponding difluoroalkylated azines. Additionally, our protocol...

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Bibliographic Details
Published inTetrahedron Vol. 159; pp. 134020 - 134026
Main Authors Ohki, Hugo, Komatsuda, Masaaki, Kondo, Hiroki, Yamaguchi, Junichiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.06.2024
Elsevier
Subjects
Chemistry
Chemistry, Organic
Fluorination
Heteroarenes
Heterocycles
Physical Sciences
Pyridines
Science & Technology
Pyridines
Heterocycles
Fluorination
Heteroarenes
OXIDATIVE ACTIVATION
BONDS
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Summary:We have developed a novel ring-opening difluorination process for pyrazoloazines. Utilizing 2.5 equivalents of Selectfluor®, this method enables electrophilic difluorination and subsequent ring-opening of pyrazoloazines, yielding the corresponding difluoroalkylated azines. Additionally, our protocol extends to the decarbonylative difluorination of pyrazoloazines when starting with a formyl group at the C3 position, demonstrating the versatility and broad applicability of this approach. This advancement in difluorination chemistry offers a new pathway for the synthesis of difluorinated compounds, potentially enriching the toolkit for practitioners in medicinal chemistry and materials science. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2024.134020