80993-27-7Relevant academic research and scientific papers
Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents
Hudson, Harry R.,Tajti, ádám,Bálint, Erika,Czugler, Mátyás,Karaghiosoff, Konstantin,Keglevich, Gy?rgy
, p. 1446 - 1455 (2020/03/16)
A series of N-benzhydryl protected α-aminophosphonates with α-phenyl, α-(1-naphtyl), α-(9-anthryl) or α-(1-pyrenyl) substituents was synthesized by the Kabachnik–Fields condensation of diphenylmethylamine (benzhydrylamine), the corresponding aryl aldehyde and a dialkyl phosphite under MW irradiation. X-ray studies performed at low temperatures for a few of these α-aminophosphonates confirmed the presence of unusually short intramolecular Cα–Hδ+ ··· δ+H–Cperi contacts.
Unexpected non-stability of aminophosphonates: Limitation of their synthesis using diphenylmethylamine procedure
Zon,Miziak,Rychlewski,Gancarz
, p. 2023 - 2030 (2008/09/18)
New diethyl 1-diphenylmethylaminoalkylphosphonates from aldehydes, ketones, diphenylmethylamine and diethyl phosphite were obtained. Their stability in acidic media as determined by 31P NMR spectroscopy strongly depends on the basicity of the nitrogen atom. The bulky N-substituent can drastically decrease the stability of the ester during acidic hydrolysis leading to decomposition products in the retro Kabachnik-Fields like reaction.
1-Amino-1-aryl- and 1-amino-1-heteroaryl-methanephosphonic acids and their n-benzhydryl-protected diethyl esters: Preparation and characterization
Hudson, Harry R.,Lee, Rosalind J.,Matthews, Ray W.
, p. 1691 - 1709 (2007/10/03)
N-Benzhydryl-protected diethyl esters of 1-amino-1-aryl- (phenyl, cumyl, p-dimethylaminophenyl, piperonyl, 1′-naphthyl, 9′-anthryl, 1′-pyrenyl) and 1-amino-1-heteroaryl- (furyl, 2′-thienyl, 3′-thienyl, 2′-pyrrolyl)-methanephosphonic acids, prepared by the
Inhibitors of phenylalanine ammonialyase: 1-aminobenzylphosphonic acids substituted in the benzene ring
Zoń, Jerzy,Amrhein, Nikolaus,Gancarz, Roman
, p. 9 - 21 (2007/10/03)
Dextrorotatory 1-amino-3′,4′-dichlorobenzylphosphonic acid was found to be a potent inhibitor of the plant enzyme phenylalanine ammonia-lyase both in vitro and in vivo from among the ring-substituted 1-aminobenzylphosphonic acids and other analogues of phenylglycine. A structure activity relationship analysis of the results obtained permits predictions on the geometry of the pocket of the enzyme and is a basis in the strategy of better inhibitor synthesis.
Reactions of hydrophosphoryl compounds with Schiff bases in the presence of CdI2
Kabachnik,Ternovskaya,Zobnina,Beletskaya
, p. 480 - 483 (2007/10/03)
The reaction of hydrophosphoryl compounds with aldimines and ketimines in the presence of catalytic amounts of cadmium iodide was investigated. A simple preparative method for the synthesis of α-aminophosphonates, phosphinates, and tertiary phosphine oxid
Facile synthesis of α-amino phosphonates in water using a Lewis acid- surfactant-combined catalyst
Manabe, Kei,Kobayashi, Shu
, p. 669 - 670 (2007/10/03)
Three-component reactions of aldehydes, amines and triethyl phosphite were efficiently catalyzed by scandium tris(dodecyl sulfate) at ambient temperature in water to give various α-amino phosphonates in high yields.
Synthesis of 1-Aminoalkane Phosphonic Acids via Benzhydrylic Schiff Bases
Issleib, Kurt,Doepfer, Klaus-Peter,Balszuweit, Arno
, p. 1392 - 1394 (2007/10/02)
A simple synthesis of 1-aminoalkanephosphonic acids is described.The addition of diethylphosphite to alkylidene- and arylidenebenzhydrylamines yields the N-benzhydryl-1-aminoalkanephosphonic acid esters.The title compounds are formed by treatment of the N-blocked esters with hydrobromic acid.The starting amine can be recycled from the hydrylbromide. - Key words: 1-Aminoalkane Phosphonic Acids, Benzhydrylic, Schiff Bases
