160598-45-8Relevant articles and documents
Synthesis of N1-arylidene-N2-quinolyl- and N2-acrydinylhydrazones as potent antimalarial agents active against CQ-resistant P. falciparum strains
Gemma, Sandra,Kukreja, Gagan,Fattorusso, Caterina,Persico, Marco,Romano, Maria P.,Altarelli, Maria,Savini, Luisa,Campiani, Giuseppe,Fattorusso, Ernesto,Basilico, Nicoletta,Taramelli, Donatella,Yardley, Vanessa,Butini, Stefania
, p. 5384 - 5388 (2006)
A series of N1-arylidene-N2-quinolyl- and N2-acrydinylhydrazones were synthesized and tested for their antimalarial properties. These compounds showed remarkable anti-plasmodial activity in vitro especially against chloroquine-resistant strains. Their pot
Direct Catalytic Reductive N-Alkylation of Amines with Carboxylic Acids: Chemoselective Enamine Formation and further Functionalizations
Trillo, Paz,Adolfsson, Hans
, p. 7588 - 7595 (2019/08/20)
Direct reductive N-alkylation of secondary amines with carboxylic acids using molybdenum hexacarbonyl (5 mol %) as catalyst and diethoxymethylsilane as reducing agent generate enamines in a straightforward fashion in high yields. The formed enamines are without the need for isolation or purification further reacted with trimethylsilyl cyanide in the same reaction flask to yield α-amino nitriles in good yields. In the optimized reaction conditions equimolar amounts of carboxylic acid and amine are reacted under neat conditions, and a catalytic amount of trifluoroethanol (0.1 mol %) is added along with TMSCN for the cyanation step. The reductive N-alkylation reaction is demonstrated to be highly chemoselective, tolerating a multitude of different functional groups present in the starting carboxylic acids and amines. The reaction is scalable and the generated α-amino nitriles are converted to other useful compounds, e.g., α-amino acids or amino-tetrazoles. In addition, the intermediate enamines are further transformed into triazolines, sulfonylformamidines, pyrimidinediones, and TMS-propargylamines, respectively, in high yields under mild reaction conditions. Benzoic acids react with secondary amines under similar conditions to give tertiary amines in high yields, and using this methodology, the biologically active compound Piribedil was isolated in 80% yield in a direct one-pot reaction setup.
Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source
Alam, Rauful,Molander, Gary A.
supporting information, p. 2680 - 2684 (2018/05/22)
The direct reductive amination of aromatic aldehydes has been realized using a photocatalyst under visible light irradiation. The single electron oxidation of an in situ formed aminal species generates the putative α-amino radical that eventually delivers the reductive amination product. This method is operationally simple, highly selective, and functional group tolerant, which allows the direct synthesis of benzylic amines by a unique mechanistic pathway.
