Synthesis of Some New 3-Pyrrolidinylquinoline Derivatives via 1,3-Dipolar Cycloaddition of Stabilized Azomethine Ylides to Quinolinyl α,β- Unsaturated Ketones

International audienceN-Metallated azomethine ylide generated from methyl (E)-N-benzylideneglycinate, LiBr and triethylamine underwent cycloaddition to quinolyl α,β- unsaturated ketones with excellent diastereoselectivity to afford new functionalised 3-pyrrolidinylquinoline derivatives

An Efficient and Recycling Catalyst for the One-Pot Three-Component Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones

Abstract: The Biginelli one-pot three-component cyclocondensation was applied in this work to prepare 3,4-dihydropyrimidinone and its analogues using the first derivative of lead, Pb(NO 3 ) 2 , as a recycling catalyst, from a diversity of aromatic aldehydes, β-ketoesters and urea. The reaction was carried out in refluxing acetonitrile and afforded the target molecules in good to excellent yields. The method offers several advantages including high yields of the products, short reaction times and easy experimental workup procedure

(3RS,4SR)-Methyl 4-(2-chloro-5,8-di­methoxy­quinolin-3-yl)-1-phenyl­pyrrolidine-3-carboxyl­ate

The mol­ecule of the title compound, C23H23ClN2O4, contains a quinolyl unit linked to a functionalized pyrrolidine system with a 3,4-trans arrangement of the substituents. The unit cell contains two stereoisomers that have the absolute stereochemistry 3S,4R and 3R,4S. The pyrrolidine ring adopts a twist conformation with pseudo-rotation parameters P = 258.2 (3)° and τ(M) = 35.3 (1)°. The packing is stabilized by C—H⋯π inter­actions and offset π–π stacking (centroid-to-centroid distance = 3.849 Å, inter­planar distance = 3.293 Å and slippage = 1.994 Å) between phenyl rings, leading to a two-dimensional network

A Convenient Access to Biquinoline Carbaldehydes using Nickel-Phosphine Complex-Mediated Homocoupling of Haloquinoline Carbaldehydes in One-Pot Reaction

Abstract: The homocoupling of 2-chloro-carbaldehyde derivatives gave the corresponding 2,2'-biquinolines by using the in situ generated reactive reagent Ni[(PPh 3 )] 4 . Several new 2-chloro-3-(1.3 dioxalan-2yl) quinoline derivatives are synthesized and structurally characterized. The overall structures of biquinoline derivatives are not planar

A one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base

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PHYTOCHEMICAL CONSTITUENTS, PHENOLIC CONTENTS, AND ANTIOXIDANT ACTIVITY OF CRATAEGUS AZAROLUS EXTRACTS

 Objective: The aim of this study was the isolation and identification of secondary metabolites from Crataegus azarolus (L.) and the antioxidant evaluation of its extracts and compounds.Methods: The air-dried powdered parts of the plant were extracted with 70% methanol and fractionated by chloroform, ethyl acetate, and n-butanol. The n-butanol extract was separated using polyamide SC6 column and silica gel TLC. In addition, a fraction of silica gel column of the CHCl3 extract was analyzed by gas chromatography–mass spectrometer (GC–MS). The total phenolic and total flavonoid contents of CHCl3 and n-butanol extracts were estimated. Furthermore, the antioxidant activities of CHCl3, n-butanol extracts, and two flavonoids were evaluated according to five different methods.Results: Eight compounds were identified in CHCl3 and n-butanol extracts, among them, five volatile compounds identified by GC–MS for the 1st time from the species, as well as three known flavonol glycosides identified by spectral analysis (ultraviolet,1H-nuclear magnetic resonance [NMR], and13C-NMR) and by comparison with literature data. The n-butanol extract showed the higher content of polyphenols (307.33 ± 2.33 mg (gallic acid equivalents)/g extract) and flavonoids (143.0 ± 2.12 mg QE/g extract) and it proves the highest antioxidant activity with all assays used.Conclusion: Five volatile compounds were identified for the 1st time from the C. azarolus and the antioxidant potential of plant extracts was measured using five different methods

Flavonoids from Algerian propolis

The investigation of propolis collected from Jijel, located in the northern-east part from Algeria afforded five flavones: pectolinarigenin (1), pilosin (2), ladanein (3), Chrysin (4) and apigenin (5). The structures were elucidated by spectroscopic analysis, including mass spectrometry, 1D and 2D NMR

One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid-catalyzed Hantzsch three-component reaction

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1, 3-Dipolar cycloaddition of stabilized azomethine ylides to alkenyl quinolines: An efficient route to polyfunctionalized 3-pyrrolidinylquinoline derivatives

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