98583-81-4Relevant academic research and scientific papers
Iron-Catalyzed Intramolecular C-H Amination of α-Azidyl Amides
Zhao, Xiaopeng,Liang, Siyu,Fan, Xing,Yang, Tonghao,Yu, Wei
, p. 1559 - 1563 (2019)
Iron-catalyzed intramolecular C-H amination of aliphatic azides has recently emerged as a powerful tool for the preparation of nitrogen heterocycles. This paper reports that α-azidyl amides can be converted in high efficacy to imidazolinone compounds via intramolecular C(sp3)-H amination by the action of a simple catalytic system composed of FeCl2 and a β-diketiminate ligand. The reactions provide a simple and atom-economical approach toward polysubstituted imidazolinones.
Electrochemistry of 2-Bromo-2-methylpropanamides. Reduction Mechanism and Cyclocoupling Reaction with Amide Solvents
Maran, Flavio,Vianello, Elio,D'Angeli, Ferruccio,Cavicchioni, Giorgio,Vecchiati, Giorgio
, p. 33 - 39 (2007/10/02)
The electrochemical reduction of series of secondary and tertiary α-bromoisobutyramides has been studied in dipolar aprotic solvents.A carbanion is formed at the mercury electrode as a consequence of two-electron C-Br bond cleavage.Voltammetry and macroelectrolysis point to a self-protonation mechanism, the carbanion undergoing protonation by a parent molecule to yield the isobutyramide.Concurrently, tertiary 2-bromoamides undergo 1,2-elimination to yield an αβ-unsaturated amide, while secondary 2-bromoamides are deprotonated at the nitrogen atom, affording a bromo-containing anion.The decay of the latter is strongly dependent on the solvent and the substituent at nitrogen.In acetonitrile, elimination and fragmentation products are identified in the electrolysed solution.On the other hand, in N,N-dimethylformamide or N,N-dimethylacetamide, the bromo-containing anion is eventually cyclocondensed onto the carbonyl group of the amide solvent, to yield an oxazolidin-4-one derivative.Preliminary data suggest that an analogous cyclocoupling reaction takes place when the reduction is carried out in 1-methyl-2-pyrrolidone.
