A KSO-mediated three-component protocol has been developed for the construction of 3-trifluoroalkylated quinoxalin-2(1)-ones under metal-free conditions. The present reaction could be accomplished through the trifluoroalkylation of quinoxalin-2(1)-ones with unactivated alkenes and Langlois' reagent (CFSONa), which provided a highly attractive approach to access a series of biologically important 3-trifluoroalkylated quinoxalin-2(1)-ones.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.9b03505DOI Listing

Publication Analysis

Top Keywords

trifluoroalkylation quinoxalin-21-ones
8
quinoxalin-21-ones unactivated
8
unactivated alkenes
8
alkenes langlois'
8
langlois' reagent
8
3-trifluoroalkylated quinoxalin-21-ones
8
metal-free trifluoroalkylation
4
quinoxalin-21-ones
4
reagent kso-mediated
4
kso-mediated three-component
4

Similar Publications

Visible-Light-Mediated Trifluoroalkylation of Isoquinolines via Three-Component Minisci-Type Reaction.

Org Lett

October 2024

C-H Activation & Phytochemistry Lab, Chemical Technology Division, CSIR-IHBT, Palampur 176061, India.

A sustainable photocatalytic approach has been established for trifluoroalkylation of isoquinoline via a three-component Minisci-type reaction using a green solvent. The polarity reversal radical cascade strategy renders the selective addition of an electrophilic CF radical to an olefin to forge a nucleophilic -centered radical. This multicomponent approach is operationally simple and environmentally benign with various functional groups, viz.

View Article and Find Full Text PDF

Herein, we disclose a direct and powerful strategy for the synthesis of highly valuable α-trifluoromethylamine and -trifluoroethylamine derivatives from a visible-light-promoted -selective heteroarylation of -trifluoroethyl hydroxylamine reagents with quinoxalin-2(1)-ones under ambient conditions. The chemoselectivity of the process (trifluoroalkylation or -trifluoroethylamination) can easily be dictated and modulated by a selection of -trifluoroethyl hydroxylamine substrates. The key to success is the protecting group on the N atom of hydroxylamine reagents, which can control the process of 1,2-H shift of the in situ-generated trifluoroethyl radical.

View Article and Find Full Text PDF

Electrochemical trifluoroalkylation/annulation for the synthesis of CF-functionalized tetrahydroquinolines and dihydroquinolinones.

Org Biomol Chem

November 2023

Institute of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China.

Tuning the electronic structure of protecting groups on the nitrogen atom of substrates has emerged as an effective strategy to achieve the tandem trifluoromethylation/C(sp)-H annulation using Langlois' reagent as the CF source for the electrochemical synthesis of functionalized tetrahydroquinolines and dihydroquinolinones.

View Article and Find Full Text PDF

Emerging as a powerful tool for lead optimization in pharmaceutical research and development, to develop the facile, general protocols that allows the incorporation of fluorine-containing motif in drug candidates has accumulated enormous research interest in recent years. Among these important motifs, the incorporation of strategic motif CF on aliphatic chain especially with the concomitant construction of trifluoromethylated alkanes bearing a CF-substituted stereogenic carbon, is of paramount importance. Herein, we disclose an asymmetric nickel-catalyzed reductive trifluoroalkylation of alkenyl halides for enantioselective syntheses of diverse α-trifluoromethylated allylic alkanes, offering a general protocol to access the trifluoromethyl analogue to chiral α-methylated allylic alkanes, one of the most prevalent key components among natural products and pharmaceuticals.

View Article and Find Full Text PDF

Fluorinated motifs are frequently encountered in drugs and agrochemicals. Incorporating fluorine-containing motifs in drug candidates for lead optimization in pharmaceutical research and development has emerged as a powerful tool. The construction of molecules that feature a trifluoromethyl (CF-) group on a stereogenic carbon has accumulated broad research efforts.

View Article and Find Full Text PDF

Want 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!