α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles

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.

Авторы
Muzalevskiy V.M. 1 , Sizova Z.A.1 , Panyushkin V.V.1 , Chertkov V.A.1 , Nenajdenko V.G. 1 , Khrustalev V.N. 2, 3
Язык
Английский
Статус
Опубликовано
Год
2021
Организации
  • 1 Department of Chemistry|M. V. Lomonosov Moscow State University
  • 2 Peoples' Friendship University of Russia
  • 3 N. D. Zelinsky Institute of Organic Chemistry of Ras
Дата создания
16.12.2021
Дата изменения
16.12.2021
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/80393/
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