Add time:07/12/2019 Source:sciencedirect.com
This paper reports one-pot synthesis of 2,2,2-trifluoroethyl 1H-pyrazole-5(3)-carboxylates via cyclocondensation of 1,1,1-trichloro-4-alkoxy-3-alken-2-ones [Cl3CC(O)C(R2) = C(R1)OMe, where R1 = H, CH3, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, −(CH2)2Ph, 4-ClC6H4, 4-BrC6H4 and R2 = H] and 1,1,1-trichloro-2,4-alkanediones, 1-aryl-4,4,4-trichloro-1,3-butanediones [Cl3CC(O)CHR2C(O)R1, where R1 = H, CH3, −(CH2)2Ph, Ph, 4-FC6H4, 4-BrC6H4, R2 = H, R1 = Ph and R2 = CH3 and R1, R2 = cyclo-(CH2)5-] with hydrazine hydrochloride in 2,2,2-trifluoroethanol (TFE). Considering the low nucleophilicity of TFE in relation to methanol or ethanol, the results provide evidence for the mechanism of hydrolysis of the trichloromethyl group attached to the 1H-pyrazol ring.
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