- 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
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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.
- Kaboudin, Babak,Kazemi, Foad,Hosseini, Narges Kadkhoda
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- Synthesis of α-amino phosphonates catalyzed by copper-based metal organic frameworks
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In this paper we report a novel and straightforward method for the synthesis of α-amino phosphonates via three-component reaction of amines, aldehydes, and triethyl phosphite in the presence of Cu2(BDC)2DABCO (Cu-MOF) as a recyclable heterogeneous catalyst. The chemical structures of the all synthesized compounds were confirmed by NMR, IR and CHN analysis.
- Larijani, Kambiz,Mokhtari, Javad,Zandieh, Haniyeh
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- Synthesis and crystal structure of phosphonic acid and bisphosphoramidate derivatives: QSAR studies of their anti-fungal potential on Macrophomina Phaseolina (Tassi) Goid
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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.
- 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
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p. 1591 - 1606
(2021/01/07)
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- Design and preparation of HPW-anchored magnetic carbon nitride nanosheets: an efficient and eco-friendly nanocomposite for one-pot synthesis of α-amino phosphonates
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Heterogeneous catalysis is one of the fastest and greatest developing branches and longstanding challenges in academic researchers and the chemical industry. Carbon-based material with various functional groups, the most abundant elements, and the main component in natural products provide a unique platform for heterogeneous catalysis due to their excellent biocompatibility and high performance. Herein, we introduce a novel nanocomposite comprising of different acids anchored to magnetic mesoporous carbon nitrides through a grindstone method to enhance nanocomposite catalysts’ environmentally benign capability. As a result, the obtained porous magnetic catalysts show the highest possible activity and product selectivity for facile preparation of α-amino phosphonates derivatives in good to excellent yields at ambient temperature. This fast and straightforward methodology offers pot economy for the satisfactory reaction of various aldehyde, amine, and triaryl and trialkyl phosphite with a broad range of functional groups in a gram scale under mild reaction conditions.
- Azhdari, Asieh,Azizi, Najmedin
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p. 4915 - 4928
(2021/07/28)
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- Niobium pentoxide, a recyclable heterogeneous solid surface catalyst for the synthesis of α-amino phosphonates
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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.].
- Sahani, Anita,Rao, Ramana Sreenivasa,Vadakkayil, Adithya,Santhosh, Murugesan,Mummoorthi, Mahalingam,Karthick, Muthupandi,Ramanathan, Chinnasamy Ramaraj
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- Catalyst free one-pot synthesis of α-aminophosphonates in aqueous ethyl lactate
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An highly efficient and environmentally friendly process for the synthesis of α-aminophosphonates has been devised, through a one-pot three-component condensation of various aldehydes, amines and triethyl phosphate in water-ethyl lactate under ultrasonic
- Gao, Ge,Chen, Meng-Nan,Mo, Li-Ping,Zhang, Zhan-Hui
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p. 528 - 532
(2019/01/04)
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- Reusable zinc oxide nanoflowers for the synthesis of α-aminophosphonates under solvent-free ultrasonication
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A simple wet chemical method is used to prepare zinc oxide nanoflowers (ZnO NFs) which were subjected to various characterization techniques such as XRD, FTIR, UV–Vis, FE-SEM, and XPS. XRD pattern indicates pure, crystalline, and monodispersed form with hexagonal wurtzite phase. The 3-D flower shape morphology with hexagonal ZnO nanorods was confirmed in FE-SEM. The synthesized ZnO NFs was used to study catalytic behavior in Kabachnik–Fields reaction under controlled ultrasound cavitation technique. High surface-to-volume ratio of ZnO NFs and the effect of ultrasonication enhances the yield of α-aminophosphonate. The catalyst was recycled and reused four times without any significant loss of its catalytic activity. Moreover, existing method becomes attractive and practical due to its easy, clean, fast, cost-effective, and eco-friendly procedure.
- Rasal, Sarika,Jain, Shilpa,Shimpi, Navinchandra G
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supporting information
p. 2420 - 2434
(2018/08/29)
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- Formic acid catalyzed one-pot synthesis of α-aminophosphonates: an efficient, inexpensive and environmental friendly organocatalyst
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Abstract: Aqueous formic acid is used for the synthesis of α-aminophosphonates through Kabachnik–Fields reaction applying aromatic amine, phosphite, and carbonyl compounds. Using formic acid as an efficient and low-cost organocatalyst provides environmental friendly, high yields, low reaction time and mild reaction condition. The isolated products were analyzed by IR, NMR, and mass techniques. Graphical abstract: [Figure not available: see fulltext.].
- Azarnia Mehraban, Jamshid,Jalali, Mahsa Sadat,Heydari, Akbar
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p. 2215 - 2223
(2018/08/04)
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- Radical Cation Salt-initiated Aerobic C?H Phosphorylation of N-Benzylanilines: Synthesis of α-Aminophosphonates
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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.
- Jia, Xiaodong,Liu, Xiaofei,Yuan, Yu,Li, Pengfei,Hou, Wentao,He, Kaixuan
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supporting information
p. 1911 - 1914
(2018/07/31)
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- Sulfated polyborate catalyzed Kabachnik-Fields reaction: An efficient and eco-friendly protocol for synthesis of α-amino phosphonates
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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.
- Khatri, Chetan K.,Satalkar, Vardhan B.,Chaturbhuj, Ganesh U.
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supporting information
p. 694 - 698
(2017/01/25)
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- 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
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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.
- Esmaeilpour, Mohsen,Zahmatkesh, Saeed,Javidi, Jaber,Rezaei, Elahe
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p. 530 - 537
(2017/05/01)
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- A Green Approach to the Synthesis of α-Amino Phosphonate in Water Medium: Carbene Insertion into the N-H Bond by Cu(I) Catalyst
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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.
- Ramakrishna, Kankanala,Thomas, Jisha Mary,Sivasankar, Chinnappan
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p. 9826 - 9835
(2016/11/02)
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- Synthesis of α-aminophosphonates using carbon nanotube supported imidazolium salt-based ionic liquid as a novel and environmentally benign catalyst
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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.
- Boroujeni, Kaveh Parvanak,Shirazi, Elham Rezazadeh,Doroodmand, Mohammad Mahdi
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p. 683 - 688
(2016/05/09)
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- Clean procedure for the synthesis of A-aminophosphonates catalyzed by choline-based ionic liquid
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A sulfated choline-based ionic liquid [Ch-OSO3H] was prepared and used as a novel catalyst for the synthesis of α-aminophosphonates via a one-pot three-component reaction with aldehydes, amines, and triethyl phosphite/diethyl phosphite at room temperature under solvent-free conditions or in aqueous media. The reaction was completed in short times and products could be simply separated from the reaction mixture in good to excellent yields. The catalyst could be recycled and reused for several times without noticeably reducing catalytic activity.
- Peng, Huan,Sun, Siyu,Hu, Yulin,Xing, Rong,Fang, Dong
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p. 215 - 223
(2015/05/27)
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- Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik-Fields reaction under solvent-free condition
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Zirconocene bis(perfluorobutanesulfonate) [Cp2Zr(OSO 2C4F9)2·2H2O] was successfully synthesized by treatment of Cp2ZrCl2 with C4F9SO3Ag, and was found to have the nature of air-stability, water tolerance, high thermal stability and strong Lewis acidity. This complex showed high catalytic efficiency for the synthesis of α-aminophosphonates via Kabachnik-Fields reaction of aldehydes/ketones, amines and diethyl phosphite under mild and solvent-free conditions. Furthermore, it can be reused without loss of activity in a test of five cycles. Compared with our previously reported complex of Cp2Zr(OSO 2C8F17)2·3H 2O·THF, this complex showed better catalytic activity.
- Li, Ningbo,Wang, Xie,Qiu, Renhua,Xu, Xinhua,Chen, Jinyang,Zhang, Xiaohong,Chen, Sihai,Yin, Shuangfeng
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p. 184 - 187
(2013/11/19)
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- Fluorous bis(oxazolines) ligand: Synthesis and application in Kabachnik-Fields reaction
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A novel fluorous bis(oxazolines) ligand was synthesized with 70% overall yield in 5 steps starting from 5-aminoisophthalic acid. The ligand was applied in the one-pot synthesis of α-aminophosphonates via copper-catalyzed Kabachnik-Fields reaction, giving the corresponding products in moderate to excellent yields under mild conditions. Furthermore, the fluorous ligand could be easily recovered and reused for four times without significant loss of activity.
- Wang, Hongjun,Deng, Tao,Cai, Chun
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p. 144 - 150
(2015/03/05)
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- Highly efficient one-pot synthesis of α-aminophosphonates catalyzed by ytterbium triflate in water
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A facile one-pot, three-component synthesis of α-aminophosphonates catalyzed by ytterbium triflate [Yb(OTf)3] in water using polyoxyethanyl α-tocopheryl sebacate (PTS) as amphiphile has been developed. The catalytic system could be readily recycled and reused several times without significant loss in its activity.
- Shen, Minggui,Shang, Shibin,Song, Zhanqian,Wang, Dan,Rao, Xiaoping,Gao, Hong,Wang, Juan
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p. 361 - 367
(2014/01/06)
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- Ultrasound mediated synthesis of α-aminophosphonates and 3,4-dihydropyrimidin-2-ones using graphene oxide as a recyclable catalyst under solvent-free conditions
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Graphene oxide is utilized as an environmentally friendly and efficient catalyst for an ultrasound mediated multi-component coupling reaction that involves aldehyde, amine/ethylacetoacetate and diethyl phosphite/urea, under solvent-free conditions, leading to the bioactive α-aminophosphonates and 3,4-dihydropyrimidin-2-ones with excellent yield. This journal is
- Bhattacharya, Tamalika,Majumdar, Biju,Dey, Deepa,Sarma, Tridib K.
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p. 45831 - 45837
(2015/02/19)
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- T3P-promoted Kabachnik-Fields reaction: An efficient synthesis of α-aminophosphonates
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A simple and efficient synthesis of α-aminophosphonates has been developed via the one-pot three-component reactions of aldehydes, amines, and trialkyl phosphites. The reactions occurred rapidly at room temperature in the presence of 1 equiv of propylphosphonic anhydride (T3P) as the condensing agent, and the α-aminophosphonate products were obtained in high yields.
- Milen, Mátyás,ábrányi-Balogh, Péter,Dancsó, András,Frigyes, Dávid,Pongó, László,Keglevich, Gy?rgy
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supporting information
p. 5430 - 5433
(2013/09/23)
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- Nano-TiO 2: An eco-friendly and clean reusable heterogeneous catalyst for preparation of α-aminophosphonates under ambient and solvent-free conditions
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A one-pot catalytic three-component synthesis of α-aminophosphonates from arylaldehydes, anilines, and triethylphosphite by employing TiO2 nanoparticles as a catalyst is described. Nano-TiO2 has been found to be an excellent catalyst for the green synthesis of α-aminophosphonates under ambient and solvent-free conditions. This green and mild nano catalytic procedure showed good recyclability and provides cleaner conversion in a short reaction time. These advantages make the protocol feasible and economically attractive for researchers.
- Shaterian, Hamid Reza,Farbodeh, Javad,Mohammadnia, Majid
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supporting information
p. 850 - 854
(2013/08/23)
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- Magnetic nanoparticles coated by acidic functionalized poly(amidoamine) dendrimer: Effective acidic organocatalyst
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A novel magnetic Br?nsted acid catalyst was synthesized based on growing poly(amidoamine) dendrimers on the surface of magnetic nanoparticles. After the dendronizing process, the MNP coated PAMAM was functionalized by chlorosulfuric acid to form an acid catalyst. Because of dendrimer coating of MNPs, catalyst shows good loading level of acidic groups on the surface. Also zwitterion nature of catalyst surface improves the catalytic activity. This new catalyst is proven to be highly effective in the synthesis of α-aminophosphonate compounds in a green way.
- Pourjavadi, Ali,Hosseini, Seyed Hassan,Hosseini, Seyedeh Talieh,Aghayeemeibody, Seyyed Alireza
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- NbCl5: An efficient catalyst for one-pot synthesis of α-aminophosphonates under solvent-free conditions
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NbCl5 has been found to be a very effective catalyst for the synthesis of a variety of α-aminophosphonates through the Kabachnik-Fields reaction of carbonyl compound, amine and diethyl phosphite under solvent-free conditions. Copyright
- Hou, Jun-Tao,Gao, Jian-Wu,Zhang, Zhan-Hui
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experimental part
p. 47 - 53
(2011/09/14)
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- Nano Fe3O4 as magnetically recyclable catalyst for the synthesis of α-aminophosphonates in solvent-free conditions
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The three component, one-pot synthesis of α-aminophosphonates has been achieved using super magnetic nano iron oxide at 50°C under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, magnetically recyclable catalyst, and solvent-free reaction conditions.
- Reddy, B.V. Subba,Krishna, A. Siva,Ganesh,Kumar, G.G.K.S. Narayana
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experimental part
p. 1359 - 1362
(2011/03/21)
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- A facile synthesis of α-aminophosphonates catalyzed by ytterbium perfluorooctanoate under solvent-free conditions
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Three-component reactions of aldehydes, amines and diethyl phosphite are efficiently catalyzed by ytterbium perfluorooctanoate [Yb(PFO)3] under solvent-free conditions, giving the corresponding α- aminophosphonates in good to excellent yields. The catalyst can be recovered and reused for several times without any significant loss of activity. Furthermore, a possible mechanism for this transformation is also presented.
- Tang, Jun,Wang, Limin,Wang, Wenbo,Zhang, Liang,Wu, Shengying,Mao, Dan
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experimental part
p. 102 - 106
(2011/03/23)
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- Nano ceria catalyzed synthesis of α-aminophosphonates under ultrasonication
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A simple, efficient and general method has been developed for the one-pot three component syntheses of α-aminophosphonates. The condensation of aldehyde, amine and triethyl phosphite by employing CeO2 nanoparticles as catalyst gave α-aminophosphonates. The catalyst showed good recyclability. Nano CeO2 has been found to be an excellent catalyst for the green synthesis of α-aminophosphonates under ultrasound irradiation and solvent-free condition. The α-aminophosphonates are obtained in good to excellent yield. This catalyst provides cleaner conversion, short reaction time and high selectivity which makes the protocol feasible and economical attractive.
- Agawane, Sandeep M.,Nagarkar, Jayashree M.
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experimental part
p. 3499 - 3504
(2011/07/08)
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- Xanthan sulfuric acid as an efficient biodegradable and recyclable catalyst for the one-pot synthesis of α-amino phosphonates
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A convenient and efficient procedure for the synthesis of α-amino phosphonates by a one-pot, three-component condensation of aldehydes, amine, and diethyl phosphite in the presence of xanthan sulfuric acid as a bio-supported catalyst under solvent-free conditions has been developed. A wide range of α-amino phosphonates have been obtained in high to excellent yields. Furthermore, the catalyst can be recovered simply and reused several times in subsequent reactions.
- Sun, Guo-Ying,Hou, Jun-Tao,Dou, Jing-Jie,Lu, Jun,Hou, Yong-Jie,Xue, Tuo,Zhang, Zhan-Hui
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experimental part
p. 1315 - 1320
(2011/10/07)
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- Tin(II) compounds as catalysts for the Kabachnik-fields reaction under solvent-free conditions: Facile synthesis of α -aminophosphonates
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In the presence of a catalytic amount of tin(II) salts, the three-component Kabachnik-Fields reaction involving aldehydes, amines, and diethyl phosphite proceeded smoothly to afford the corresponding -aminophosphonates in good to high yields. These reactions were carried out under solvent-free conditions.
- Gallardo-Macias, Ricardo,Nakayama, Kensaku
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experimental part
p. 57 - 62
(2010/04/26)
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- SO3H-functionalized ionic liquids catalyzed the synthesis of α-aminophosphonates in aqueous media
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SO3H-functionalized halogen-free ionic liquids were prepared and used as efficient and recyclable catalysts for the synthesis of α-aminophosphonates at room temperature via the one-pot three-component condensation reaction in aqueous media with good yields of 80-96%. The postprocessing was simple, and the catalysts could be reused at least six times without noticeably decreasing the catalytic activity.
- Fang, Dong,Jiao, Changmei,Ni, Chunjie
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experimental part
p. 546 - 550
(2011/07/08)
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- PPh3-catalysed one-pot three-component syntheses of α-aminophosphonates under solvent-free conditions
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A simple and efficient preparation of α-aminophosphonates under relatively mild conditions by the one-pot reaction of aldehydes with amines and dialkyl phosphites using catalytic amounts of triphenylphosphine is described.
- Tian, You-Ping,Xu, Feng,Wang, Yi,Wang, Jian-Jun,Li, Hui-Li
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experimental part
p. 78 - 80
(2009/10/02)
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- Syntheses of substituted 8-(aminobenzyl)dinaphthodioxaphosphocine 8-oxides
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Substituted (8-aminobenzyl)dinaphthodioxaphosphocine 8-oxides were prepared in a two-step process. The first step of the reaction is one-pot synthesis of α-aminophosphonates by the reaction of aldehydes, amines, and trialkyl phosphite in the presence of ceric ammonium nitrate. The second step is cyclization of α-aminophosphonates with bis(2-hydroxy-1-naphthyl)methane in the presence of a catalytic amount of p toluenesulphonic acid under reflux conditions. Their structures were established by elemental analyses, IR, 1H, 13C, 31P NMR, and mass spectral data.
- Babu, M. F. Stephen,Babu, B. Hari,Reddy, K. R. Kishore Kumar,Raju, C. Naga,Reddy, C. Suresh
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p. 1336 - 1341
(2008/09/19)
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- Metal triflate-catalyzed one-pot synthesis of α-aminophosphonates from carbonyl compounds in the absence of solvent
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A simple and general method has been developed for one-pot three-component synthesis of α-aminophosphonates catalyzed by several metal inflates [M(OTf)n, M = Li, Mg, Al, Cu, Ce] in the absence of solvent in good to high yields.
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara
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p. 2692 - 2696
(2007/10/03)
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