7473-93-0Relevant articles and documents
Successive oxidation-condensation reactions using a multifunctional gold-supported nanocomposite (Au/MgCe-HDO)
Chandra, Ramesh,Kumar, Loveneesh,Kumar, Rupesh,Sehrawat, Hitesh,Tomar, Ravi,Verma, Nishant
, p. 3472 - 3481 (2022/02/21)
The application of gold-supported nanocomposites is useful in clinical diagnostics because of their ability to provide bio-compatible and sensitive detection systems. A gold-supported magnesium hydroxide and cerium oxide nanocomposite framework (Au/MgCe-HDO) was synthesized and characterized via XRD, XPS, SEM, DLS, TEM, and TGA techniques. The nanocomposite was used as a selective catalyst for the aerobic oxidation of alcohols under mild reaction conditions followed by successive condensation reactions, like Knoevenagel and Claisen-Schmidt condensation. Substituted benzyl alcohols were converted into the corresponding carbonyl compounds in the presence of the Au/MgCe-HDO nanocomposite with O2 gas and toluene as a solvent. We observed that, upon the addition of malononitrile/ethyl cyanoacetate/acetophenone to the catalyst in the aerobic oxidation reaction, the reaction proceeds to produce the corresponding desired condensation product with up to 95% yield.
Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio
supporting information, p. 4876 - 4894 (2021/09/20)
Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.
Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B
Iacovino, Luca G.,Pinzi, Luca,Facchetti, Giorgio,Bortolini, Beatrice,Christodoulou, Michael S.,Binda, Claudia,Rastelli, Giulio,Rimoldi, Isabella,Passarella, Daniele,Di Paolo, Maria Luisa,Dalla Via, Lisa
supporting information, p. 1151 - 1158 (2021/06/30)
A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.
