A highly efficient [3 + 2] cycloaddition between trifluoromethylated N-acylhydrazones and nitroolefins in the presence of potassium hydroxide under phase transfer catalysis is developed to afford potentially bioactive trifluoromethylated pyrazolidines, which can be further transformed into trifluoromethylated pyrazoles in good yields.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c7ob01299c | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks.
Beilstein J Org Chem
November 2023
Department of Fire Protection Engineering, China Fire and Rescue Institute, Beijing 102202, P. R. of China.
Nitrogen-containing organofluorine derivatives, which are prepared using fluorinated building blocks, are among the most important active fragments in various pharmaceutical and agrochemical products. This review focuses on the reactivity, synthesis, and applications of fluoromethylated hydrazones and acylhydrazones. It summarizes recent methodologies that have been used for the synthesis of various nitrogen-containing organofluorine compounds.
View Article and Find Full Text PDFChiral-Boron-Complex-Catalyzed Asymmetric [3 + 2] Cycloaddition of β-Trifluoromethyl α,β-Unsaturated Ketones with '-Cyclic Azomethine Imines.
J Org Chem
December 2023
Pingyuan Laboratory, State Key Laboratory of Antiviral Drugs, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
The ()-3,3'-(3,5-(CF)-CH)-BINOL-boron-complex-catalyzed asymmetric 1,3-dipolar cycloaddition of β-trifluoromethyl α,β-unsaturated ketone with '-cyclic azomethine imines was developed to afford '-bicyclic pyrazolidine derivatives bearing a stereogenic carbon center containing CF motifs in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, and >99% ee). This catalytic system features mild reaction conditions, high efficiency, and a broad substrate scope.
View Article and Find Full Text PDFSynthesis of Trifluoromethylated Pyrazolidines, Pyrazolines and Pyrazoles via Divergent Reaction of β-CF-1,3-Enynes with Hydrazines.
Org Lett
October 2021
Department of Chemistry, School of Chemistry and Molecular Engineering, East China Normal University, 500. Dongchuan Road, Shanghai, 200241, People's Republic of China.
Three types of trifluoromethylated pyrazolidines, pyrazolines, and pyrazoles can be synthesized via divergent reaction of β-CF-1, 3-enyne with hydrazines. The reaction with simple hydrazine monohydrate or sulfonyl hydrazines as nucleophiles produces 1,3,4-trisubstituted pyrazolines, whereas the reaction with acetyl hydrazine as nucleophiles affords 1,4,5-trisubstituted pyrazolidines. Using phenylhydrazine or -butylhydrazine as a reaction partner, the products are easily oxidized to form 1,4,5-trisubstituted pyrazoles.
View Article and Find Full Text PDFSynthesis of trifluoromethylated pyrazolidines by [3 + 2] cycloaddition.
Org Biomol Chem
August 2017
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. China. and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
A highly efficient [3 + 2] cycloaddition between trifluoromethylated N-acylhydrazones and nitroolefins in the presence of potassium hydroxide under phase transfer catalysis is developed to afford potentially bioactive trifluoromethylated pyrazolidines, which can be further transformed into trifluoromethylated pyrazoles in good yields.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!