New one-pot and regioselective method for the synthesis of 3-trifluoromethyl-1H-1-phenylpyrazoles

New one-pot and regioselective method for the synthesis of 3-trifluoromethyl-1H-1-phenylpyrazoles

Pittaluga, Everton P.; (PQ)*, Helio G. Bonacorso; Correa, Michele S.; Porte, Liliane M. F.; Junges, Andrizia F.; Martins, Marcos A. P.; Zanatta, Nilo

Abstract:

Pyrazoles derivatives has been extensively explored by our research group contemplating their biological activities. Efficient approaches to introduce a CF3 group at the C-3 position of pyrazole ring in a regioselective manner has been getting attention, mostly because these compounds often show pharmacological activities such as the antiinflammatory Celecoxib® and the anticoagulant Razaxaban® and the anticoagulant Razaxaban®. So, we report an efficient and regioselective insertion of a CF3 group into pyrazole rings from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH =CR1(OR) where R = Me or Et, R1 = H, Me, Ph, 2-Furyl and R1-R2 = -C4H8-] (1a-e) and 1-phenylsemicarbazide (2) in order to obtain 3-trifluoromethyl- 1-phenylpyrazoles (3a-e) as the main isomer.

Pyrazoles derivatives has been extensively explored by our research group contemplating their biological activities. Efficient approaches to introduce a CF3 group at the C-3 position of pyrazole ring in a regioselective manner has been getting attention, mostly because these compounds often show pharmacological activities such as the antiinflammatory Celecoxib® and the anticoagulant Razaxaban® and the anticoagulant Razaxaban®. So, we report an efficient and regioselective insertion of a CF3 group into pyrazole rings from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH =CR1(OR) where R = Me or Et, R1 = H, Me, Ph, 2-Furyl and R1-R2 = -C4H8-] (1a-e) and 1-phenylsemicarbazide (2) in order to obtain 3-trifluoromethyl- 1-phenylpyrazoles (3a-e) as the main isomer.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013925215748

Referências bibliográficas

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Como citar:

Pittaluga, Everton P.; (PQ)*, Helio G. Bonacorso; Correa, Michele S.; Porte, Liliane M. F.; Junges, Andrizia F.; Martins, Marcos A. P.; Zanatta, Nilo; "New one-pot and regioselective method for the synthesis of 3-trifluoromethyl-1H-1-phenylpyrazoles", p-287-287. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013925215748