1341165-10-3Relevant academic research and scientific papers
α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles
Muzalevskiy, Vasiliy M.,Sizova, Zoia A.,Panyushkin, Vasiliy V.,Chertkov, Vyacheslav A.,Khrustalev, Victor N.,Nenajdenko, Valentine G.
, p. 2385 - 2405 (2021/02/01)
An efficient pathway toward a novel class of trifluoromethyl building blocks was elaborated. The reaction of α-CF3-enamines with arylaldehydes resulted in direct synthesis of α,β-diaryl-CF3-enones isolated in up to 93% yield as E-isomers. The possible reaction mechanism was proposed using the Zimmerman-Traxler model. The reaction of α,β-diaryl-CF3-enones with hydrazines opens a novel pathway to trifluoromethylated pyrazolines. Oxidation of pyrazolines with DDQ opened access to totally regioselective preparation of 3-CF3-pyrazoles isolated in high yield. Using this strategy, 4-arylated derivatives of known drugs Celebrex, Mavacoxib, and SC-560 can be synthesized.
Mechanistic study of multi-step nucleophilic substitution for trifluoromethylated styrenes
Rulev, Alexander Yu.,Ushakov, Igor A.,Kondrashov, Evgeniy V.,Muzalevskiy, Vasiliy M.,Shastin, Aleksey V.,Nenajdenko, Valentine G.
experimental part, p. 945 - 950 (2011/11/05)
The key steps of the reactions of nitrogen nucleophiles with β-halogen-β-trifluoromethylstyrenes have been studied by 19F and 1H NMR monitoring and quantum-chemical calculations. In contrast to the mechanism proposed earlier for nucl
