91010-46-7Relevant academic research and scientific papers
Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations
Campbell, Joanna L. P.,Davies, Christopher D.,Ho?ek, Jan,Ko?ovsky, Pavel,Kysilka, Ond?ej,Popov, Kirill K.,Pour, Milan
, p. 920 - 943 (2022/01/27)
Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys
Aminophosphinic acids in a pyridine series: Cleavage of pyridine-2- and pyridine-4-methyl(amino)phosphinic acids in acidic solutions
Boduszek, Bogdan,Olszewski, Tomasz,Goldeman, Waldemar,Konieczna, Magdalena
, p. 787 - 795 (2007/10/03)
The synthesis of a series of new pyridine aminomethylphosphinic acids is described. These compounds were obtained in the reaction of the corresponding pyridine aldehydes with primary amines and with ethyl phenylphosphinate, or methylphosphinate, in the presence of bromotrimethylsilane. In aqueous, strong acid solutions, pyridine aminophosphinic acids were split, forming the phenyl-, or methylphosphonic, acid and the corresponding secondary pyridyl-alkylamines. The kinetics of some observed cleavages were measured, and a mechanism of the cleavage has been proposed. Copyright Taylor & Francis Group, LLC.
Aminophosphine oxides in a pyridine series. Studies on the cleavage of pyridine-2- and pyridine-4-yl-(N-benzylamino)-methyldiphenylphosphine oxides in acidic solutions
Goldeman, Waldemar,Olszewski, Tomasz K.,Boduszek, Bogdan,Sawka-Dobrowolska, Wanda
, p. 4506 - 4518 (2007/10/03)
The synthesis and reactions of 1-(N-benzylamino)-1-(2-pyridyl)- and 1-(N-benzylamino)-1-(4-pyridyl)-methyldiphenylphosphine oxides are described. It was found that these compounds were exceptionally easy to cleave in aqueous sulfuric acid solutions to form diphenylphosphinic acid and the corresponding N-(pyridylmethyl)-benzylamines. The structure of a single diastereoisomer, that is, the (R)-(+)-1-[N-(α-methylbenzylamino)]-1-(4-pyridyl)-(S)-methyldiphen ylphosphine oxide was determined by X-ray crystallography. The acidic alcoholysis of the selected model chiral pyridine aminophosphine oxides was investigated by means of 31P NMR spectroscopy. The cleavage kinetics were also studied. On the basis of the obtained results, a mechanism of the cleavage was formulated.
The acidic cleavage of pyridylmethyl(amino)phosphonates. Formation of the corresponding amines
Boduszek, Bogdan
, p. 12483 - 12494 (2007/10/03)
Hydrolysis of 3-pyridylmethyl(amino)phosphonates by means of 20% aq. hydrochloric acid gave corresponding 3-pyridimethyl(amino)phosphonic acids, as expected. However, hydrolysis of 2- and 4-pyridylmethyl(amino)phosphonates led to decomposition of the phosphonates with a cleavage of C-P bond and formation of the corresponding amines. The leaving phosphorus moiety was identified as phosphoric acid. The scope of the reaction is limited to 2- and 4-pyridylmethyl derivatives of aminophosphonic acids and their esters, as well as to the derivatives possessing similar structure. On the contrary, the basic hydrolysis of 2- and 4-pyridylmethyl(amino)phosphonates led to the corresponding monoalkyl esters of the aminophosphonates, and no cleavage of C-P bond was observed in those cases.
