18137-67-2Relevant academic research and scientific papers
Catalytic antioxidant activity of bis-aniline-derived diselenides as GPx mimics
Barbosa, Flavio A. R.,Bettanin, Luana,Botteselle, Giancarlo V.,Braga, Antonio L.,Canto, R?mulo F. S.,Ciancaleoni, Gianluca,Domingos, Josiel B.,Elias, Welman C.,Gallardo, Hugo,Rafique, Jamal,Saba, Sumbal,Salin, Drielly N. O.
supporting information, (2021/08/06)
Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium.
A One-Pot Access to Benzo[b][1,4]selenazines from 2-Aminoaryl Diselenides
Menichetti, Stefano,Capperucci, Antonella,Tanini, Damiano,Braga, Antonio L.,Botteselle, Giancarlo V.,Viglianisi, Caterina
supporting information, p. 3097 - 3102 (2016/07/14)
Different 2-sulfonylaminoaryl diselenides substituted with electron-withdrawing or -donating groups are transformed in one pot into benzo[b][1,4]selenazines. The reaction uses a substoichiometric amount of Cu(OTf)2, and the mechanism involves a base-mediated 1,4-elimination at selenium with the generation of an o-iminoselenoquinone and a 2-sulfonylaminoselenolate anion. The former is a dienic species that can react with electron-rich dienophiles to give the target cycloadducts. The latter is oxidised by air back to the starting diselenide, allowing its complete consumption. A preliminary investigation of the GPx-like activity of a selected selenazine is also described.
Direct synthesis of 2-aryl-1,3-benzoselenazoles by reaction of bis(2-aminophenyl) diselenides with aryl aldehydes using sodium metabisulfite
Radatz, Cátia Schwartz,Alves, Diego,Schneider, Paulo Henrique
, p. 1316 - 1321 (2013/02/23)
We present here a general and easy method for the synthesis of several 2-aryl-1,3-benzoselenazoles from the reaction of bis(2-aminophenyl) diselenides with different aryl aldehydes, promoted by the non-toxic inorganic reducing agent sodium metabisulfite (Na2S2O5) in DMSO at 120 °C. This efficient method furnishes in high yields the corresponding 2-aryl substituted 1,3-benzoselenazoles and tolerates a range of substituents at the aryl ring of aldehydes. The use of focused microwave irradiation decreases drastically the reaction time from 48 to 2 h.
Catalytic oxidative domino degradation of alkyl phenols towards 2- and 3-substituted muconolactones
Giurg, Miroslaw,Kowal, Ewa,Muchalski, Hubert,Syper, Ludwik,Mlochowski, Jacek
experimental part, p. 251 - 266 (2009/04/07)
The catalytic oxidative domino degradation of phenols was investigated. Hydrogen peroxide (30% aq.) was used as an oxidant and 2,2′-dinitro-4, 4′-ditrifluoromethyldiphenyl diselenide 4e as a catalyst. The products were muconic acid 5, and muconolactones muconolactones - 5-carboxymethylfuran- 2(5H)-ones 7 and 9. Phenols with alkyl groups at 2 or 4 positions of the benzene ring were converted regioselectively to corresponding muconolactones substituted at alkenylene ring carbon atoms. The reaction mechanism is proposed. Copyright Taylor & Francis Group, LLC.
