Refernces
10.1002/aoc.3682
The research focuses on the development of a novel, green, and efficient catalytic system using zinc cation supported on λ-carrageenan magnetic nanoparticles (Zn2+/λ-carrageenan/Fe3O4) for the one-pot three-component synthesis of quinoline derivatives. The study involves the preparation of the catalyst through a series of steps, including the synthesis of nanomagnetite, coating it with λ-carrageenan, and decorating it with zinc cation. The catalyst's structure and properties were characterized using various techniques such as FT-IR spectroscopy, FE-SEM, EDX, TEM, XRD, VSM, TGA, and ICP analysis. The experiments involved a model reaction of benzaldehyde, aniline, and butanal, optimized for catalyst amount, solvent, and temperature, and then extended to a series of reactions with different substituted aldehydes and anilines. The analyses confirmed the successful synthesis of the catalyst and its high activity in the green synthesis of 16 quinoline derivatives with high yields, without the use of toxic solvents or co-catalysts.
10.1021/jo00064a043
The study focuses on the synthesis and conformational analysis of a quinoline derivative (1), which is an orally active inhibitor of 5-lipoxygenase and a leukotriene antagonist. The key chemicals involved include 2-(chloromethyl)quinoline (4) and the substituted phenol 12, which are coupled in the final step to form the target compound. The phenol derivative 12 is synthesized from m-hydroxyacetophenone (8) through an aldol condensation with n-butyraldehyde, yielding an intermediate that is subsequently reduced to 12. The synthesis of 2-(chloromethyl)quinoline (4) involves converting quinaldine (2) to its N-oxide monohydrate (3) and then reacting it with benzenesulfonyl chloride. The final coupling of 4 and 12 is performed in DMF with anhydrous potassium carbonate as a base, yielding the desired compound 1 in high purity. The study also includes an X-ray crystallographic analysis and molecular mechanics computations to elucidate the conformation of the synthesized compound, revealing a structure where the quinoline and benzenoid rings are nearly perpendicular, providing insights into its potential therapeutic applications.
10.1007/BF00702401
The research aimed to investigate the stereo- and regioselectivity of radical addition reactions involving isopropanol and n-butanal to the chiral compound (5R)-5-(1-menthyloxy)furan-2(5H)-one. The study utilized photochemical decomposition of tert-butyl peroxide (TBP) to initiate the radical addition, resulting in high regio- and diastereoselective formation of the adducts. The absolute configurations of the products were determined through comparison of proton spin-spin coupling constants with molecular mechanics calculations. The results confirmed that the radical addition occurred specifically at position 4 of the furanone ring, with the substituents in the products being trans-arranged relative to each other.
10.1021/jo00253a029
The research investigates the formation of 1,3,5-trisubstituted 1,2,4-triazoles through cation radical-induced oxidative cycloaddition of arylhydrazones of benzaldehyde and butyraldehyde to various nitriles. The study aims to explore the mechanism and efficiency of this reaction pathway, comparing it with other known methods. Key chemicals used include thianthrenyl perchlorate (Th'+C104-) and tris(2,4-dibromophenyl)aminium hexachloroantimonate (Ar3N'+SbC16-) as cation radical oxidants, and aceto-, propio-, and acrylonitrile as nitrile substrates. The results show that the cation radical-induced reactions yield 1,2,4-triazoles with high efficiency, and the formation of 5-vinyltriazoles instead of 5-cyano-2-pyrazolines indicates that the reaction does not proceed through nitrilimines, as previously thought. This finding distinguishes the cation radical route from other documented cycloadditions and highlights its potential as a useful method for synthesizing 1,2,4-triazoles.
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