| Autor: |
Muzalevskiy VM; Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia., Sizova ZA; Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia., Panyushkin VV; Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia., Chertkov VA; Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia., Khrustalev VN; Peoples' Friendship University of Russia, Moscow 117198, Russia.; N. D. Zelinsky Institute of Organic Chemistry of RAS, 47 Leninsky Prospect, Moscow 119991, Russia., Nenajdenko VG; Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia. |
| Abstrakt: |
An efficient pathway toward a novel class of trifluoromethyl building blocks was elaborated. The reaction of α-CF 3 -enamines with arylaldehydes resulted in direct synthesis of α,β-diaryl-CF 3 -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-CF 3 -enones with hydrazines opens a novel pathway to trifluoromethylated pyrazolines. Oxidation of pyrazolines with DDQ opened access to totally regioselective preparation of 3-CF 3 -pyrazoles isolated in high yield. Using this strategy, 4-arylated derivatives of known drugs Celebrex, Mavacoxib, and SC-560 can be synthesized. |
