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.
Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis
Chen, Dong-Huang,Sun, Wei-Ting,Zhu, Cheng-Jie,Lu, Guang-Sheng,Wu, Dong-Ping,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 8827 - 8831 (2021/03/16)
The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.
Nucleophilic Imines and Electrophilic o-Quinone Methides, a Three-Component Assembly of Assorted 3,4-Dihydro-2 H-1,3-benzoxazines
Chen, Peishan Kc,Wong, Yuk Fai,Yang, Derek,Pettus, Thomas R. R.
supporting information, p. 7746 - 7749 (2019/10/11)
A one-pot method for joining three separate components leading to an assortment of N-substituted 3,4-dihydro-2H-1,3-benzoxazines is described. The method involves the addition of a Grignard reagent to an o-OBoc salicylaldehyde in the presence of an imine. With a variety of components, 15 examples are presented, including the diastereoselective incorporation of chiral imines.