ω-(3-Trifluoromethylpyrazol-4-yl)alkanoic acids via (3+2)-cycloaddition of nitrile imines with cyclic enones and deacylative aromatization

被引：2

作者：

Kowalczyk, Anna ^{[1
]}

Utecht-Jarzynska, Greta ^{[1
]}

Jasinski, Marcin ^{[1
]}

机构：

[1] Univ Lodz, Fac Chem, Tamka 12, PL-91403 Lodz, Poland

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2023年 / 272卷

关键词：

Trifluoromethylpyrazoles; Alkanoic acids; Nitrile imines; (3+2)-cycloadditions; Deacylations; Fluorinated heterocycles; PROMOTED 3+2 CYCLOADDITION; TRIFLUOROACETONITRILE IMINES; DERIVATIVES; INHIBITORS; PYRAZOLES; CHLORIDES; ACCESS;

D O I：

10.1016/j.jfluchem.2023.110206

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of omega-substituted alkanoic acids functionalized with 1-aryl-3-trifluoromethylpyrazol-4-yl group was synthesized via two-step protocol using in situ generated CF3-nitrile imines and cyclic enones as key building blocks. The first 1,3-dipolar cycloaddition step proceeded in a fully selective manner either in solutions or under solvent-free mechanochemical activation. Treatment of the first formed cycloadducts derived from 2-cyclopentenone or 2-cyclohexenone with DDQ afforded corresponding bicyclic pyrazoles formed via dehydrogenative oxidation pathway, whereas MnO2-mediated deacylative aromatization led to desired propionic or butyric acid derivatives, respectively. In contrast, oxidation of model 2-cycloheptenone-derived (3 + 2)-cycloadduct yielded bicyclic analogue irrespectively to the applied conditions.

引用

页数：9

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