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

Autor:	Vasiliy V. Panyushkin, Zoia A. Sizova, Valentine G. Nenajdenko, Vyacheslav A. Chertkov, Vasiliy M. Muzalevskiy, Victor N. Khrustalev
Rok vydání:	2021
Předmět:	Reaction mechanism Mavacoxib Trifluoromethyl 010405 organic chemistry Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Yield (chemistry) medicine medicine.drug
Zdroj:	The Journal of Organic Chemistry. 86:2385-2405
ISSN:	1520-6904 0022-3263
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6dace37dbcce4d3e02796b6210ed6284 https://doi.org/10.1021/acs.joc.0c02516 Zobrazit plný text záznamu