63000-01-1Relevant academic research and scientific papers
Synthesis of α-Aminophosphonate Derivatives by Microwave-Assisted Kabachnik-Fields Reaction
Bálint, Erika,Fazekas, Eszter,Tripolszky, Anna,Kangyal, Réka,Milen, Mátyás,Keglevich, Gy?rgy
, p. 655 - 659 (2015)
The synthesis of aminophosphonates was studied in aqueous solution using triethyl phosphite and under solvent-free and microwave-assisted conditions using >P(O)H species and starting from primary amines or α-, β- and γ-amino acid derivatives. The synthesis of bisaminophosphonates from suitable bifunctional compounds was also investigated in the presence of the T3P reagent.
Visible-Light Mediated Photooxidative Phosphorylation of Benzylamines: A Novel and Mild Pathway Towards α-Aminophosphorus Compounds
Ung, Sosthène P.-M.,Perepichka, Inna,Li, Chao-Jun
, (2021/12/09)
Traditional syntheses of α-aminophosphorus therapeutic targets proceed through the hydrophosphorylation of C=N or C=O bonds, thus necessitating preliminary oxidized substrates. Cross-dehydrogenative coupling strategies can bypass this extra oxidation step by oxidizing simpler substrates in situ before phosphorylating them, but those protocols can suffer from the use of toxic stoichiometric oxidants. Photochemical strategies can access those oxidized intermediates without any harsh conditions and can use molecular oxygen as a benign and sustainable oxidant. We report herein a simple protocol using visible light, phosphinylidenes and benzylamine derivatives for the synthesis of α-aminophosphorus products under aerobic conditions and using an iridium photosensitizer.
Synthesis of novel α-hydroxyphosphonates along with α-aminophosphonates as intermediates
Belovics, Alexandra,H?gele, Gerhard,Keglevich, Gy?rgy,Varga, Petra R.
, (2021/12/22)
New phosphoryl α-hydroxyphosphonates, their acylated derivatives, as well as α-aminophosphonates were synthesized as potentionally biologycally active substrates. The reverzible formation of α-hydroxyphosphonates allowing a few interesting side-reactions was also observed.
Magnetic ZnO?CuO?Iron ore nanocomposites as a green and highly efficient heterogeneous nanocatalyst for solventless synthesis of α-aminophosphonates
Sajadi, S Mohammad
, p. 25 - 30 (2019/11/14)
A green novel synthesis of ZnO?CuO?Iron ore nanocomposites as a novel and magnetic heterogeneous nanocatalyst is used for the one-pot synthesis of α-aminophosphonates under solventless conditions. This study benefits from the magnetic iron ore acting as a multi-mineral Lewis acid system, the green properties and the large surface area due to its nanostructure. Moreover, scanning electron microscope analysis confirmed that the nanocatalyst gave an excellent yield and good recyclability; which, even after the 10th cycle of the model reaction retained its potential with no significant loss of catalytic activity.
A green one-pot three-component synthesis of α-aminophosphonates under solvent-free conditions and ultrasonic irradiation using Fe3O4@SiO2-imid-PMAn as magnetic catalyst
Esmaeilpour, Mohsen,Zahmatkesh, Saeed,Javidi, Jaber,Rezaei, Elahe
, p. 530 - 537 (2017/05/01)
An efficient and environment friendly process for the synthesis of α-aminophosphonates has been devised. Through a one-pot three-component condensation of various aldehydes, amines, and triethyl phosphite in the presence of Fe3O4@SiO2-imid-PMAn nanoparticles as magnetic catalysts under solvent-free conditions and ultrasonic irradiation, α-aminophosphonates were obtained with excellent yields. The reactions under solvent-free conditions at room temperature are compared with the ultrasonic-assisted reactions. This new procedure has notable advantages such as short reaction time, excellent yields, easy purification, and the absence of any tedious workup or purification. The aforementioned catalyst could be easily recovered by an external magnetic field and can be reused for six consecutive reaction cycles without significant loss of activity. In addition, SEM and DLS of the catalyst after the reaction cycle were investigated.
Sulfated polyborate catalyzed Kabachnik-Fields reaction: An efficient and eco-friendly protocol for synthesis of α-amino phosphonates
Khatri, Chetan K.,Satalkar, Vardhan B.,Chaturbhuj, Ganesh U.
supporting information, p. 694 - 698 (2017/01/25)
An efficient, and environmentally benign protocol for a three-component Kabachnik-Fields reaction of aldehydes, amines, and diethyl phosphite catalyzed by sulfated polyborate has been described to afford α-amino phosphonates under solvent-free reaction conditions. The major advantages of the present method are high yields, short reaction time, simple work-up procedure, inexpensive, eco-friendly and reusable catalyst and solvent-free reaction conditions and tolerance towards various functional groups present in the substrates.
Synthesis of fluorescent aminophosphonates by green chemistry procedures
Ku?nierz, Anna,Chmielewska, Ewa
, p. 700 - 705 (2017/06/05)
Fluorescent aminophosphonates were obtained using optimized conditions of the microwave-stimulated Kabachnik-Fields reaction. Unfortunately, in the case of more demanding, bulky amines and aldehydes this reaction failed to give the desired products.
Synthesis of α-aminophosphonates using carbon nanotube supported imidazolium salt-based ionic liquid as a novel and environmentally benign catalyst
Boroujeni, Kaveh Parvanak,Shirazi, Elham Rezazadeh,Doroodmand, Mohammad Mahdi
, p. 683 - 688 (2016/05/09)
A supported acidic catalyst was easily prepared via anchoring imidazolium salt-based ionic liquid onto multiwalled carbon nanotube by covalent bonds. This novel immobilized acidic ionic liquid effectively catalyzed the one-pot synthesis of α-aminophosphonates from the reaction of amines and aldehydes with diethyl phosphite. The catalyst can be easily recovered and reused without appreciable change in its efficiency.
Highly efficient synthesis of α-aminophosphonates catalyzed by hafnium(IV) chloride
Li, Xiao-Chuan,Gong, Shan-Shan,Zeng, De-Yun,You, Yue-Hai,Sun, Qi
supporting information, p. 1782 - 1785 (2016/04/05)
A highly efficient one-pot method for the synthesis of a variety of α-aminophosphonates via the one-pot three-component reaction of aldehyde, amine, and phosphite has been developed using only 2 mol % HfCl4 as the catalyst. The NMR evidence strongly indicated the catalytic roles of Hf(IV) on the activation of aldehyde, phosphite, and imine intermediate.
Tandem catalysis of amines using porous graphene oxide
Su, Chenliang,Tandiana, Rika,Balapanuru, Janardhan,Tang, Wei,Pareek, Kapil,Nai, Chang Tai,Hayashi, Tamio,Loh, Kian Ping
supporting information, p. 685 - 690 (2015/01/30)
Porous graphene oxide can be used as a metal-free catalyst in the presence of air for oxidative coupling of primary amines. Herein, we explore a GO-catalyzed carbon-carbon or/and carbon-heteroatom bond formation strategy to functionalize primary amines in tandem to produce a series of valuable products, i.e., α-aminophosphonates, α-aminonitriles, and polycyclic heterocompounds. Furthermore, when decorated with nano-Pd, the Pd-coated porous graphene oxide can be used as a bifunctional catalyst for tandem oxidation and hydrogenation reactions in the N-alkylation of primary amines, achieving good to excellent yields under mild conditions.
