128474-65-7Relevant 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
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.
Platinum(II) complexes containing aminophosphonate esters: Synthesis, characterization, cytotoxicity and action mechanism
Huang, Ke-Bin,Chen, Zhen-Feng,Liu, Yan-Cheng,Li, Zhu-Quan,Wei, Jian-Hua,Wang, Meng,Xie, Xiao-Li,Liang, Hong
, p. 554 - 561 (2013/07/11)
New platinum(II) complexes containing aminophosphonate ester were synthesized and fully characterized, which were found to possess better solubility in both organic solvents and water than cisplatin. These platinum(II) complexes exhibited considerable cyt
Application of bromotrimethylsilane and trialkyl phosphites for convenient and effective synthesis of aminophosphonic acids and corresponding monoalkyl and dialkyl esters
Boduszek
, p. 663 - 672 (2007/10/03)
Application of bromotrimethylsilane (Br-TMS) in a mixture with trialkyl phosphite for synthesis of various aminophosphonic acids and esters was investigated. It was found, that appropriate mixtures of Br-TMS and trimethyl phosphite or triethyl phosphite were effective reagents for phosphorylation of various aldimines, obtained from aromatic and heteroaromatic aldehydes. Products of these reactions were corresponding aminophosphonic acids, or corresponding dialkyl or monoalkyl esters, respectively.
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.
Synthesis of Derivatives of (1R*,10aR*)-1-Azido-10-benzylidene-4-(diethylphosphono)-1,2,10,10a-tetrahydro-2-oxo-4H-azeto(1,2-a)pyrido(1,2-d)pyrazin-9-ylium Bromide
Hakimelahi, Gholam H.,Sardarian, Ali R.
, p. 180 - 184 (2007/10/02)
The synthesis of some derivatives of the title compound VI is described.Bromination of diethyl(cis-3-azido-2-oxo-4-styrylazetidin-1-yl)(pyridin-2-yl)methylphosphonate (6) in MeOH gave tricyclic β-lactam 7, while similar bromination of diethyl(cis-3-azido-2-oxo-4-vinylazetidin-1-yl)(pyridin-2-yl)methylphosphonate (9) afforded tricyclic β-lactam 10.Mechanisms for these transformations are proposed (Schemes 1 and 2).
