22483-21-2Relevant articles and documents
Multicomponent synthesis of polyphenols and their in vitro evaluation as potential β-amyloid aggregation inhibitors
Galante, Denise,Banfi, Luca,Baruzzo, Giulia,Basso, Andrea,D’Arrigo, Cristina,Lunaccio, Dario,Moni, Lisa,Riva, Renata,Lambruschini, Chiara
, (2019)
While plant polyphenols possess a variety of biological properties, exploration of chemical diversity around them is still problematic. Here, an example of application of the Ugi multicomponent reaction to the combinatorial assembly of artificial, yet “natural-like”, polyphenols is presented. The synthesized compounds represent a second-generation library directed to the inhibition of β-amyloid protein aggregation. Chiral enantiopure compounds, and polyphenol-β-lactam hybrids have been prepared too. The biochemical assays have highlighted the importance of the key pharmacophores in these compounds. A lead for inhibition of aggregation of truncated protein AβpE3-42 was selected.
Retro-Ene Reactions of N-Substituted Derivatives of 4-Aza-2,2-dimethyl-1-phenyl-3-butenone and Related Compounds
Armesto, Diego,Horspool, William M.,Perez-Ossorio, Rafael,Ramos, Ana
, p. 3378 - 3381 (1987)
The retro-ene reactions of N-substituted derivatives of 4-aza-2,2-dimethyl-1-phenyl-3-butenone with methanol and benzylamine are described.The reactions with methanol yield methyl benzoate and N-substituted derivatives of 2-methylpropanimine.Reaction of N-benzyl-4-aza-2,2-dimethyl-1-phenyl-3-butenone with benzylamine yields N-benzyl-2-methyl-1-phenylpropanimine and N,N'-dibenzylformamidine.
Base-Free Oxidative Coupling of Amines and Aliphatic Alcohols to Imines over Au–Pd/ZrO2 Catalyst under Mild Conditions
Cui, Wenjing,Jia, Meilin,Sagala,Wang, Jiang
, p. 958 - 967 (2021/06/06)
Abstract: The base-free synthesis of imines from amines and aliphatic alcohols over Au–Pd alloy catalysts under ambient conditions was developed. A series of Au–Pd/ZrO2 bimetallic catalysts with varying metal loadings and Au?:?Pd molar ratios were prepared and their catalytic performance was investigated. The 3.0?wt?% Au–Pd/ZrO2 alloy catalyst with Au?:?Pd molar ratio of 1?:?1 showed the best catalytic performance. Under air atmosphere, various imines were obtained from coupling of amines and aliphatic alcohols without any additives or promoters. The performance of alloy NPs was superior to that of monometallic catalysts due to the synergistic effect which was demonstrated by TEM, XPS, and UV–Vis characterization. Our work suggested this transformation differed slightly from those reactions between amine and benzyl alcohol and a possible mechanism was proposed. Moreover, the Au–Pd/ZrO2 catalyst could be easily separated and reused for at least five successive runs with high catalytic activity.
Activation of primary amines by copper(i)-based lewis acid promoters in the solventless synthesis of secondary propargylamines
Cimarelli, Cristina,Navazio, Federica,Rossi, Federico V.,Del Bello, Fabio,Marcantoni, Enrico
, p. 2387 - 2396 (2019/05/27)
Primary amines are activated by copper(I)-based Lewis acid promoters in an A 3 -coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO 4 /NaI system, a practical precursor of the in situ generated effective CuI/I 2 system, that worked well, but only in a restricted number of examples. Substitution of I 2 with CeCl 3 ·7H 2 O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.
