Details

Autor(en) / Beteiligte

• Topchiy, Maxim A.
• Zharkova, Daria A.
• Asachenko, Andrey F.
• Muzalevskiy, Vasiliy M.
• Chertkov, Vyacheslav A.
• Nenajdenko, Valentine G.
• Nechaev, Mikhail S.

Titel

Mild and Regioselective Synthesis of 3‐CF3‐Pyrazoles by the AgOTf‐Catalysed Reaction of CF3‐Ynones with Hydrazines

Ist Teil von

• European journal of organic chemistry, 2018-08, Vol.2018 (27-28), p.3750-3755

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Gold‐ and silver‐catalysed reactions of trifluoromethylated ynones with aryl (alkyl) hydrazines were investigated. The use of (THD‐Dipp)AuOTf and AgOTf resulted in quick heterocyclization reactions to selectively give 3‐CF3‐pyrazoles. AgOTf was found to be the catalyst of choice, and various 3‐CF3‐pyrazoles were formed in up to 99 % isolated yield with high regioselectivity. The reaction has a broad scope: 3‐CF3‐pyrazoles with alkyl and aryl substituents as well as different functional groups can be prepared by this approach. The known pyrazole drugs Celebrex® and SC‐560 were efficiently prepared to demonstrate the utility of the method. Mechanistic investigations revealed that the reaction involves the formation of a hemiaminal as a key intermediate. An efficient synthesis of 3‐CF3‐pyrazoles through the silver‐catalysed reaction of trifluoromethylated ynones with aryl (alkyl) hydrazines was developed. The heterocyclization took place very quickly and with high regioselectivity to give 3‐CF3‐pyrazoles in up to 99 % isolated yield. The known pyrazole drugs Celebrex® and SC‐560 were efficiently prepared to demonstrate the utility of the method.