64532-41-8Relevant academic research and scientific papers
Mandelic acid catalyzed one-pot three-component synthesis of α-aminonitriles and α-aminophosphonates under solvent-free conditions at room temperature
Kaur, Gurpreet,Shamim, Mussarat,Bhardwaj, Vaishali,Gupta, Vivek Kumar,Banerjee, Bubun
, p. 1545 - 1560 (2020)
A simple, mild, straightforward, efficient and eco-friendly protocol has been developed for the synthesis of a series of α-aminonitriles via the one-pot three-component Strecker reactions between various aldehydes, amines and trimethylsilyl cyanide using a catalytic amount of mandelic acid as a naturally occurring, low-cost, efficient organo-catalyst under solvent-free conditions at room temperature. Under the same optimized conditions synthesis of α-aminophosphonates were also achieved via the one-pot three-component Kabachnik-Fields reactions of aldehydes, amines and triethyl phosphate.
Synthesis and crystal structure of phosphonic acid and bisphosphoramidate derivatives: QSAR studies of their anti-fungal potential on Macrophomina Phaseolina (Tassi) Goid
Gholivand, Khodayar,Abbod, Mohsen,Ebrahimi Valmoozi, Ali Asghar,Barzegar, Omolbanin,Nasrollah Tabar, Hadis,Yaghoubi, Rouhollah,Hosseini, Mahdieh,Safaie, Naser,Rahimzadeh Dashtaki, Maryam,Dusek, Michal,Mani-Varnosfaderani, Ahmad
, p. 1591 - 1606 (2021/01/07)
A series of phosphonic acid and bisphosphoramidate derivatives were synthesized and characterized. The bioactivities against the fungal pathogen Macrophomina phaseolina and human acetylcholinesterase AChE enzyme were studied using QSAR based on multiple linear regression. L17, with (p-Cl–C6H4–NH) (p-Cl–C6H4)C(H)P(O)(OC2H5)2 skeleton, demonstrated a great mortality on the M. phaseolina mycelial growth by 83% inhibition at 150 mg/L; the other tested derivative showed moderate to weak antifungal activity against the fungus. QSAR model based on the GA-MLR method revealed the importance of 3D descriptors (De, Mor18e, H8m, and Mor30p) on the antifungal activity. It showed good capability in predicting the fungicidal activity of the studied molecules. Another derivative, L5, with (m-CH3–NC5H4–NH)(m-CH3–C6H4)C(H)P(O)(OCH3)2 skeleton displays the most potent anti-AChE activity. The electronic parameters, ΔEL-H, and ELUMO, have the highest contribution of human AChE. The authors suggest that these models could be usefully employed in designing more effective crop protection compounds without side effects on non-target organisms.
Niobium pentoxide, a recyclable heterogeneous solid surface catalyst for the synthesis of α-amino phosphonates
Sahani, Anita,Rao, Ramana Sreenivasa,Vadakkayil, Adithya,Santhosh, Murugesan,Mummoorthi, Mahalingam,Karthick, Muthupandi,Ramanathan, Chinnasamy Ramaraj
, (2021/02/12)
Abstract: Niobium pentoxide, a bifunctional solid surface catalyst, has been successfully employed to facilitate the three-component reaction between aldehydes, amines and triethyl phosphite at room temperature under solvent-free conditions to generate α-amino phosphonate in moderate to good yields. The catalyst can be recycled through simple filtration and reused to effect this transformation. Graphic abstract: [Figure not available: see fulltext.].
DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates
Cheng, Ming-Xing,Lei, Jing-Wei,Xie, Cai-Xia
supporting information, p. 114 - 118 (2019/01/04)
This work reports a DDQ-mediated cross-dehydrogenative-coupling reaction of secondary amines with dialkyl phosphonates under mild conditions. This reaction proceeds efficiently without involving visible light or transition-metal catalysis. This new approa
Magnetic BaFe12O19/Al2O3: An Efficient Heterogeneous Lewis Acid Catalyst for the Synthesis of α-Aminophosphonates (Kabachnik–Fields Reaction)
Piri, Tayebeh,Peymanfar, Reza,Javanshir, Shahrzad,Amirnejat, Sara
, p. 3384 - 3394 (2019/08/02)
Abstract: The design and application of environmentally friendly catalysts to reduce the quantity of toxic wastes is critical for improving?the chemical synthesis process. Therefore, BaFe12O19/Al2O3, a magnetic mesoporous nanocomposites, were designed synthesized and characterized using different techniques such as energy dispersive X-ray (EDX) spectroscopy, X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy (FESEM), Brunauer–Emmett–Teller?(BET) adsorption method, and vibrating sample magnetometry (VSM). The prepared BaFe12O19/Al2O3 display a high surface area (1773.22?m2/g) with an average pore diameter of 3.946?nm from nitrogen sorption analysis. In addition, the synthesized nanocomposites prove to be an active heterogeneous Lewis acid catalyst for the solvent free synthesis of α-aminophosphonates at ambient temperature, through three-component reaction of aldehydes/ketones, amines and triethyl phosphite. The use of this catalyst results in an effortless magnetic recoverability and recyclability, high yield and short reaction time under solvent-free conditions. Graphic Abstract: [Figure not available: see fulltext.].
Radical Cation Salt-initiated Aerobic C?H Phosphorylation of N-Benzylanilines: Synthesis of α-Aminophosphonates
Jia, Xiaodong,Liu, Xiaofei,Yuan, Yu,Li, Pengfei,Hou, Wentao,He, Kaixuan
supporting information, p. 1911 - 1914 (2018/07/31)
A radical cation salt-initiated phosphorylation of N-benzylanilines was realized through an aerobic oxidation of the sp3 C?H bond, providing a series of α-aminophosphonates in high yields. An investigation of the reaction scope revealed that this mild catalyst system is superior in good functional group tolerance and high reaction efficiency. The mechanistic study implied that the cleavage of the sp3 C?H bond was involved in the rate-determining step.
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.
A novel straightforward synthesis of α-aminophosphonates: one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a catalyst
Kaboudin, Babak,Kazemi, Foad,Hosseini, Narges Kadkhoda
, p. 4475 - 4486 (2017/07/22)
We report here a novel and straightforward synthesis method for the preparation of α-aminophosphonates in relatively good yield. The method involves the one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a recyclable catalyst. CuO@Fe3O4 nanoparticles were prepared and their structures were confirmed by the FT-IR, TGA, VSM, TEM and X-ray diffraction patterns analyses.
A Green Approach to the Synthesis of α-Amino Phosphonate in Water Medium: Carbene Insertion into the N-H Bond by Cu(I) Catalyst
Ramakrishna, Kankanala,Thomas, Jisha Mary,Sivasankar, Chinnappan
, p. 9826 - 9835 (2016/11/02)
Synthesis of amino phosphonates is more important owing to their significant applications in the biological systems. There are few methods already known in the literature to make these molecules; however, known methods have their own disadvantages. In this regard, synthesis of different kinds of amino phosphonates have been achieved via phosphonate substituted carbene insertion into the N-H bond of aniline catalyzed by readily available copper salt under mild reaction conditions in water. In order to find an efficient catalyst for carbene insertion reaction in neat water, a large number of transition metal catalysts were screened, and we found that the [Cu(CH3CN)4]ClO4 was the best catalyst under employed reaction conditions. Using this environmentally benign methodology (copper catalyzed reaction in water), a large number of biologically important amino phosphonates have been synthesized, isolated (37 examples), and characterized using standard analytical and spectroscopic techniques.
A Simple and Green Procedure for the One-Pot Synthesis of α-Aminophosphonates with Quaternary Ammonium Salts as Efficient and Recyclable Reaction Media
Yu, Ya-Qin,Xu, Da-Zhen
, p. 1869 - 1876 (2015/06/30)
A simple and highly efficient approach has been developed for a multicomponent one-pot reaction of aldehydes or ketones with amines and diethyl or triethyl phosphite to give the corresponding α-aminophosphonates. In the presence of quaternary ammonium salts, which are environmental friendly, inexpensive, and recyclable, α-aminophosphonates were obtained in excellent yields at room temperature within short times.
