272786-89-7Relevant academic research and scientific papers
Cleavage of phosphorus-carbon (P-C) bonds of α-amino phosphonates with intramolecular hydrogen migration in the gas phase using electrospray ionization tandem mass spectrometry
Gao, Yuzhen,Xu, Jian,He, Yaohui,Tang, Guo,Lin, Zhiwei,Liu, Hongxia,Gao, Xiang,Zhao, Yufen
, p. 1964 - 1970 (2014/08/18)
RATIONALE α-Amino phosphonates with intrinsic biological activities have been used in a wide variety of applications. Because of the widespread existence of natural organophosphorus compounds containing P-C bonds such as the α-amino phosphonates, it is important to investigate the gas-phase chemistry of P-C bonds in order to determine their basic properties, which might provide some insights into their biosynthesis and catalytic cleavage. METHODS Twenty α-amino phosphonates were successfully synthesized and their fragmentation behavior was systematically investigated using in-solution deuterium labeling in combination with high-resolution Fourier transform ion cyclotron resonance (FTICR) electrospray ionization tandem mass spectrometry. RESULTS The fragmentation pathways of twenty α-amino phosphonates with different chemical structures were systematically studied. In general, P-C bonds could be easily cleaved via a novel intramolecular hydrogen atom migration from the amino group to the phosphoryl group through a five-membered-ring intermediate in the gas phase. A possible mechanism of the rearrangement of α-amino phosphonates is proposed. CONCLUSIONS An interesting intramolecular hydrogen atom migration between the amino and phosphoryl groups was observed with cleavage of the P-C bond in the molecule through a five-membered-ring intermediate. This characteristic fragmentation pathway not only provides some insights into the basic chemistry of compounds with P-C bonds, but could also have some applications in the structural determination of the α-amino phosphonate analogues. Copyright
Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid as a recyclable catalyst for the kabachnik-fields reaction of isatins, imines, and aldehydes under solvent-free conditions
Nazish, Mohd,Saravanan,Khan, Noor-Ul H.,Kumari, Prathibha,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Bajaj, Hari C.
, p. 1753 - 1760 (2015/02/02)
Magnetic-nanoparticle-supported phosphotungstic acid has been used to efficiently catalyze the hydrophosphonylation reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α-hydroxy and α-amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle was proposed.
Direct transformation of amides into α-amino phosphonates via a reductive phosphination process
Gao, Yuzhen,Huang, Zhongbin,Zhuang, Rongqiang,Xu, Jian,Zhang, Pengbo,Tang, Guo,Zhao, Yufen
supporting information, p. 4214 - 4217 (2013/09/12)
The first general method for the reductive phosphination of amides in one pot has been developed. The reactions described provide a novel access to α-amino phosphonates in good to excellent yields, cover a broad scope of substrates such as secondary and tertiary amides, and do not require a low temperature.
Diversity-oriented synthesis of α-aminophosphonates: A new class of potential anticancer agents
Bhattacharya, Asish K.,Raut, Dnyaneshwar S.,Rana, Kalpeshkumar C.,Polanki, Innaiah K.,Khan, Mohd Sajid,Iram, Sana
supporting information, p. 146 - 152 (2013/10/01)
A small library of structurally diverse α-aminophosphonates has been synthesized by reacting alkyl/aryl aldehydes, alkyl/aryl amines and alkyl/aryl phosphites in one-pot catalyzed by Amberlite-IR 120 resin (acidic). All the synthesized a-aminophosphonates were assayed for their in vitro cytotoxic activities against a panel of five human cancer cell lines including A-549, NCI-H23 (Lung), Colo 320DM (Colon), MG-63 (Bone marrow) and Jurkat (Blood T lymphocytes). Compound 4n having (R)-1-phenylethanamine was found to be the most active amongst all the synthesized a-aminophosphonates against all the five cancer cell lines, most prominent being against Jurkat cell line with an IC 50 value of 4 μM. Surprisingly, compound 4o having (S)-1-phenylethanamine was found to be devoid of any cytotoxicity. Our finding suggests that these chemical entities could further serve as interesting template for the design of potential anticancer agents.
One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina
Ambica,Kumar, Satish,Taneja, Subhash C.,Hundal, Maninder S.,Kapoor, Kamal K.
, p. 2208 - 2212 (2008/09/18)
SbCl3 adsorbed on Al2O3 is found to be an efficient and recyclable catalyst in promoting three-component coupling reactions of aldehydes (aromatic and aliphatic), amines (aryl amines, aliphatic amines and esters of S-α-amino acids) and dialkylphosphites to afford the corresponding α-aminophosphonates in high yields. The ethyl ester of S-phenylalanine was observed to yield the corresponding α-aminophosphonate with S,S-diastereoisomer formed in dominance over the S,R-diastereoisomer.
Uncatalysed preparation of α-amino phosphonates under solvent free conditions
Zahouily, Mohamed,Elmakssoudi, Abdelhakim,Mezdar, Abdessamad,Rayadh, Ahmed,Sebti, Said
, p. 324 - 327 (2007/10/03)
A simple, efficient and environmentally friendly procedure has been developed for the three component coupling of carbonyl compounds, aromatic and aliphatic amines and dialkyl phosphites to produce α-amino phosphonates. The α-amino phosphonates are synthesised in high yields (74-97%) in a few minutes (1-3 min) by microwave irradiation under solvent-free conditions, avoiding the use of any catalyst.
