42222-06-0Relevant articles and documents
Identification of new biologically active synthetic molecules: comparative experimental and theoretical studies on the structure-antioxidant activity relationship of cyclic 1,3-ketoamides
Kerbadou, Riad Mustapha,Hadjadj Aoul, Ratiba,Benmaati, Aouicha,Taleb, Assya,Hacini, Salih,Habib Zahmani, Hadjira
, (2021)
Antioxidant agent is a chemical that prevents the oxidation of other chemical substances. Its use is the most effective means of protecting the organism by neutralizing the harmful effects of free radicals caused by oxidative stress. In the present work, a series of β-ketoamides containing a variety of monosubstituted amide groups were synthesized and tested as antioxidant agents. In order to establish a possible structure-antioxidant activity relationship, we are presenting a systematic theoretical study of these molecules with the aim of clarifying the active sites. In particular, we discuss the selectivity resulting from the choice of a free radical/antioxidant system. The theoretical study of these molecules was carried out using density functional theory (DFT) calculations at the B3LYP/6-311G (d,p) level of theory. In order to shed light on the antioxidant properties of β-ketoamides, O–H bond dissociation enthalpies (BDEs), ionization potentials (IPs), electron affinities (EAs), proton affinities (PAs), and electron transfer enthalpies (ETEs) are performed in the gas phase and in ethanol. The results obtained show that the HAT mechanism is thermodynamically more favored in the gas phase, while the SPLET is preferred in the polar solvent.
Eco-friendly access to β-ketoamides: One-step catalyst-and solvent-free amidation of β-ketoesters under microwave irradiation
Dechira, Khadidja,Taleb, Assya,Benmaati, Aouicha,Hacini, Salih,Zahmani, Hadjira Habib
, p. 152 - 160 (2018/03/21)
A highly efficient and facile catalyst- and solvent-free one step amidation of β-ketoesters, without using any additional reagents, is described. Therefore, β-ketoamides are obtained in good to excellent yields by condensation of β-ketoesters with various primary or secondary amines. This eco-friendly protocol has been developed under microwave irradiation.
Metal-free michael-addition-initiated three-component reaction for the regioselective synthesis of highly functionalized pyridines: Scope, mechanistic investigations and applications
Allais, Christophe,Lieby-Muller, Frederic,Rodriguez, Jean,Constantieux, Thierry
supporting information, p. 4131 - 4145 (2013/07/19)
A metal-free and completely regioselective three-component synthesis of highly functionalized pyridines from 1,3-dicarbonyl derivatives and Michael acceptors has been achieved. Activated Michael acceptors, that is, β,γ-unsaturated α-oxo carbonyl derivatives, were utilized, allowing substitution at the 4-position and remarkable functional diversity at the 2-position of the pyridine ring. The scope and limitations of this environmentally friendly domino reaction are disclosed, with full experimental data, and the results of mechanistic investigations are discussed. The three-component synthesis of polysubstituted pyridines starting from 1,3-dicarbonyl compounds, α,β-unsaturated carbonyl derivatives and ammonium acetate has been studied, including the scope and mechanism. This methodology is a rare example of a totally regioselective multicomponent access to highly substituted pyridines that complies with many of the stringent criteria of sustainable chemistry. Copyright
Ru-catalyzed asymmetric hydrogenation of 3-oxoglutaric acid derivatives via solvent-assisted pinpoint recognition of carbonyls in close chemical propinquity
Li, Wanfang,Ma, Xin,Fan, Weizheng,Tao, Xiaoming,Li, Xiaoming,Xie, Xiaomin,Zhang, Zhaoguo
supporting information; experimental part, p. 3876 - 3879 (2011/10/01)
Upon comparison of hydrogenation rates of various β-ketocarboxylic acid derivatives, β-ketoamides were found to be hydrogenated slightly faster than β-ketoesters in EtOH in the presence of [RuCl(benzene)(S)- SunPhos]Cl at 70 °C with 20 bar of hydrogen. In THF these differences were so sharpened that β-ketoamides were hydrogenated even faster than in EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.
Novel amodiaquine congeners as potent antimalarial agents
Casagrande, Manolo,Basilico, Nicoletta,Parapini, Silvia,Romeo, Sergio,Taramelli, Donatella,Sparatore, Anna
, p. 6813 - 6823 (2008/12/22)
To develop new classes of antimalarial agents, the possibility of replacing the phenolic ring of amodiaquine, tebuquine, and isoquine with other aromatic nuclei was investigated. Within a first set of pyrrole analogues, several compounds displayed high ac
Imidoylketene Imines, III. Preparation and Conformation of Vinylogous Ureas
Goerdeler, Joachim,Lindner, Christian
, p. 2499 - 2508 (2007/10/02)
A number of new β-aminocroton- and cinnamamides (3), often with 2-cyano, -keto, or -ester groups, were prepared by addition of the corresponding secondary enamines 1 to isocyanates.In the case of tert-butyl isocyanate the use of zinc chloride was helpful.
