A Direct Silver‐Catalyzed Three‐Component Approach to Trifluoromethylated Cyanopyrazoles and Cyanopyrazolines

A three‐component strategy for the synthesis of an important class of trifluoromethylated cyanopyrazoles from aldehydes, malononitrile and trifluorodiazoethane is reported. This approach involves a domino Knoevenagel condensation/1,3‐dipolar cycloaddition/dehydrocyanation process. Surprisingly, the...

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Veröffentlicht in:Advanced synthesis & catalysis 2023-07, Vol.365 (13), p.2218-2224
Hauptverfasser: Kumar, Anuj, Mathew, Shintu, Jamali, Muhammad Fahad, Ahamad, Shakir, Kant, Ruchir, Mohanan, Kishor
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Sprache:eng
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Zusammenfassung:A three‐component strategy for the synthesis of an important class of trifluoromethylated cyanopyrazoles from aldehydes, malononitrile and trifluorodiazoethane is reported. This approach involves a domino Knoevenagel condensation/1,3‐dipolar cycloaddition/dehydrocyanation process. Surprisingly, the use of cyanoacetate in place of malononitrile resulted in the formation of trifluoromethylated cyanopyrazolines. The protocol provides access to a wide variety of trisubstituted pyrazoles and pyrazolines thus expanding the chemical space for these structural units.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300322