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New one-pot, efficient, and regioselective method for the synthesis of 3-Trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs
Authors:Helio G Bonacorso  Michele S CorreaLiliane MF Porte  Everton P PittalugaNilo Zanatta  Marcos AP Martins
Institution:Núcleo de Química de Heterociclos-NUQUIMHE, Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil
Abstract:An efficient and regioselective procedure for the synthesis of a series of alkyl(aryl/heteroaryl) substituted 3-trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs, from the cyclocondensation reactions of 4-alkoxy-1,1,1-trihaloalk-3-en-2-ones CX3C(O)CR2=CR1(OMe/OEt), where R1 = H, Me, Ph, 2-Furyl; R2 = H; R1-R2 = -C4H8- and X = F, Cl] and 1-phenylsemicarbazide in an acidified alcoholic medium (R3OH/H2SO4), where R3 = Me, Et, Pri was successfully applied and is described here in detail.
Keywords:Phenylpyrazoles  3-Trifluoromethylpyrazoles  Esterification reactions  Cyclization reactions  Phenylsemicarbazides
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