135055-84-4Relevant academic research and scientific papers
Copper-catalyzed amidation of aryl iodides using KF/Al2o 3: An improved protocol
Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Mehdinejad, Hamidreza
, p. 1517 - 1520 (2004)
A mild method for the copper-catalyzed amidation of aryl iodides is reported. This simple C-N bond forming procedure shows that the combination of air stable CuI and 1,10-phenanthroline in the presence of KF/Al 2O3 comprises an extremely efficient and general catalyst system for the N-amidation of aryl iodides. Different functionalized aryl iodides were efficiently coupled with amides using this method.
Synthesis of diarylamines catalyzed by iron salts
Correa, Arkaitz,Carril, Monica,Bolm, Carsten
supporting information; experimental part, p. 10919 - 10922 (2009/11/30)
A study was conducted to demonstrate the synthesis of diarylamines catalyzed by iron salts. The study evaluated the influence acetyl as an N-protecting group. The coupling of acetanilide and iodobenzene was selected as a model reaction, to optimize the reaction conditions. It was observed that a considerable amount of the N-deprotected compound was obtained along with the desired N-acetyl diarylamine. It was also observed that diphenylamine was isolated in a significant yield, by performing a basic hydrolysis with NaOMe after the iron-catalyzed arylation. A one-pot synthesis of diphenylamine was performed by adding NaOMe to the N-arylation reaction mixture, after the acetanilide was consumed completely. It was demonstrated that the strategy overcomes the synthetic limitations associated with poor reactivity of aromatic amines under iron catalysis and serves as an alternative approach for the preparation of diarylamines.
Copper-catalyzed amidation of aryl iodides in the presence of various chelating ligands
Hosseinzadeh, Rahman,Golchoubian, Hamid,Masoudi, Mahtab
experimental part, p. 649 - 653 (2009/05/11)
N,N′-Dibenzylethylenediamine is presented as a new, efficient, and versatile bidentate ligand suitable for the copper catalyzed formation of the C-N bond. This bidentate ligand has been demonstrated to facilitate the copper catalyzed cross-coupling reactions of aryl iodides with amides to afford the desired products in good to excellent yields.
Microwave-enhanced Goldberg reaction: A novel route to N-arylpiperazinones and N-arylpiperazinediones
Lange, Jos H.M,Hofmeyer, Lovina J.F,Hout, Floris A.S,Osnabrug, Stefan J.M,Verveer, Peter C,Kruse, Chris G,Feenstra, Rolf W
, p. 1101 - 1104 (2007/10/03)
An unprecedented microwave-enhanced Goldberg reaction constitutes the key strategic step in the synthesis of N-arylpiperazinones, N-arylpiperazinediones and N-aryl-3,4-dihydroquinolinones. Microwave irradiation greatly accelerates the Goldberg reaction using NMP as solvent. Alkylation at the 3-position of the formed N-aryl-2-piperazinones furnishes new N-aryl-3-alkyl-2-piperazinones.
Sterically Hindered N-Aryl-2(1H)-Quinolones and N-Aryl-6(5H)-Phenanthridinones: Separation of Enantiomers and Barriers to Racemization
Mintas, Mhaden,Mihaljevic, Vesna,Koller, Helmut,Schuster, Doris,Mannschreck, Albrecht
, p. 619 - 624 (2007/10/02)
The novel N-aryl-4-chloro-3-methyl-2(1H)-quinolones (1)-(4) have been synthesized by condensation of the appropriate diphenylamine with diethyl methylmalonate and subsequent chlorination of the resulting N-aryl-4-hydroxy-3-methyl-2(1H)-quinolones (7)-(10). 5-(1-Naphthyl)-6(5H)-phenanthridinone (5) has been synthesized by the Chapman rearrangement of the 6-(1-naphthoxy)phenanthridine (11).Separation of the enantiomers (M) and (P) of the quinolones (1)-(4) and phenanthridinones (5), (6) was achieved by liquid chromatography on triacetylcellulose.The barriers to partial rotation about the C-N bond in (1)-(6) were determined by thermal racemization of enantiomers and are compared with those of structurally related molecules.
