- 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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- New phosphonate based corrosion inhibitors for mild steel in hydrochloric acid useful for industrial pickling processes: Experimental and theoretical approach
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The present work deals with the synthesis and study of the inhibition effect of three α-aminophosphonates, namely diethyl (((4-chlorophenyl)amino)(phenyl)methyl)phosphonate (APCI-1), diethyl (((4-chlorophenyl)amino)(4-methoxyphenyl)methyl)phosphonate (APCI-2) and diethyl (1-((4-chlorophenyl)amino)-3-phenylallyl)phosphonate (APCI-3), on mild steel corrosion in 1 M hydrochloric acid solution using both experimental and theoretical methods. Weight loss results showed that the inhibition performance of the studied compounds increases with the concentration and the maximum inhibition efficiency was obtained at just 564 × 10-6 M concentration. Among all the three tested inhibitors, APCI-3 showed the best result having an inhibition efficiency of 96.90%. The potentiodynamic polarization study indicates that these α-aminophosphonates act as mixed type inhibitors and predominantly function as a cathodic inhibitor. Adsorption of the tested APCIs on the metallic surface obeyed the El-Awady adsorption isotherm. The adsorption of these compounds on the metallic surface was also supported by the scanning electron microscopy (SEM) and atomic force microscopy (AFM) methods. A good insight about the inhibition mechanism of the tested compounds was derived using DFT based quantum chemical calculations for their neutral as well as protonated forms. The orientation of inhibitors on the metallic surface and the interaction energies of these molecules were obtained using molecular dynamic simulation studies. Both experimental and theoretical studies suggested that the inhibition efficiency of the tested compounds followed the order APCI-3 > APCI-2 > APCI-1 and well corroborated each other.
- Gupta, Neeraj Kumar,Verma, Chandrabhan,Salghi,Lgaz,Mukherjee,Quraishi
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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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- 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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- 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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- DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates
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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
- Cheng, Ming-Xing,Lei, Jing-Wei,Xie, Cai-Xia
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supporting information
p. 114 - 118
(2019/01/04)
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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 novel hydrophobic copper complex supported on γ-Fe2O3 as a magnetically heterogeneous catalyst for one-pot three-component synthesis of α-aminophosphonates
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A novel hydrophobic copper complex supported on γ-Fe2O3 is synthesized and characterized by different methods such as FT-IR, XRD, TEM, SEM, TGA, VSM, ICP and CHN analysis. It was used as a magnetically recyclable heterogeneous cataly
- Sobhani, Sara,Khakzad, Fatemeh
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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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- Benzimidazolium dicationic ionic liquid as an efficient and reusable catalyst for the synthesis of α-aminophosphonates and bis (α-aminophosphonates) under solvent-free condition
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(Chemical Equation Presented) Benzimidazolium based on dicationic acidic ionic liquid (AIL) is designed, synthesized, and successfully used as a catalyst for the one-pot synthesis of α-aminophosphonates derivatives. The application of this AIL is studied in a new one-pot method for the synthesis of α-aminophosphonates derivatives under solvent-free conditions. The advantages of thismethod are the reusability of catalyst, high conversion, short reaction time, and simple experimental procedure.
- Eshghi, Hossein,Mirzaei, Mahdi,Hasanpour, Maede,Mokaber-Esfahani, Majid
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p. 1606 - 1620
(2015/09/15)
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- A Simple and Green Procedure for the One-Pot Synthesis of α-Aminophosphonates with Quaternary Ammonium Salts as Efficient and Recyclable Reaction Media
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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.
- Yu, Ya-Qin,Xu, Da-Zhen
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p. 1869 - 1876
(2015/06/30)
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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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- 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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- An efficient and convenient procedure for the one-pot synthesis of α-aminophosphonates from aryl azides under solvent-free conditions
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A novel and simple approach to the multicomponent one-pot reaction of aldehydes, diethyl phosphite, and azides to form α-aminophosphonates under solvent-free conditions at room temperature has been developed. In the presence of iodine and iron, aryl azides were, for the first time, used as substrates for the synthesis of α-aminophosphonates. The reactions were completed within 5 minutes to 12 hours and afforded the corresponding products in good yields.
- Yu, Ya-Qin
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p. 2545 - 2550
(2013/09/24)
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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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- Gold complex-catalyzed CP bond formation by Kabachnik-Fields reactions
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CP bond formation was realized through the three-component reaction of an amine, an aldehyde and a dialkylphosphite catalyzed by gold complex. The corresponding α-aminophosphonates were afforded in one-pot reaction with high yields under mild conditions.
- Zhang, Yan,Zhu, Chengjian
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p. 134 - 137
(2013/01/14)
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- Choline chloride·2ZnCl2 ionic liquid: An efficient and reusable catalyst for the solvent free Kabachnik-Fields reaction
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The choline based Zn containing deep eutectic mixture was applied as an efficient and eco-friendly ionic liquid catalyst for the one pot three-component synthesis of α-aminophosphonates under solvent-free condition at room temperature. The reactions were completed in short times and products were obtained in good to excellent yields.
- Disale, Shamrao T.,Kale, Sandip R.,Kahandal, Sandeep S.,Srinivasan, Thandankorai G.,Jayaram, Radha V.
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experimental part
p. 2277 - 2279
(2012/07/14)
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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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- 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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- Synthesis of α-aminophosphonates using polystyrene supported Al(OTf)3 as a heterogeneous catalyst
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A mild and efficient method has been devised for the preparation of -aminophosphonates from three component condensation of an aldehyde, an amine, and diethyl phosphite in the presence of catalytic amounts of cross-linked polystyrene supported aluminium triflate (Ps-Al(OTf)3) under solvent-free conditions in good to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. Taylor & Francis Group, LLC.
- Boroujeni, Kaveh Parvanak
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experimental part
p. 173 - 176
(2011/04/25)
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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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- Thiamine hydrochloride (VB1): An efficient catalyst for one-pot synthesis of α-aminophosphonates under ultrasonic irradiation
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An efficient synthesis of novel α-aminophosphonates by the reaction of aldehydes and amines with triethyl phosphite in the presence of the easily available, inexpensive, and nontoxic catalyst thiamine hydrochloride (VB1). This method affords the α-aminophosphonates under the influence of ultrasound irradiation in aqueous medium, in short reaction times (4-6 min), high yields (85-95%), with improved purity. The process is green, mild, inexpensive and excellent yields are the main compensation of this procedure.
- Mandhane, Priyanka G.,Joshi, Ratnadeep S.,Nagargoje, Deepak R.,Gill, Charansingh H.
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experimental part
p. 563 - 566
(2012/01/06)
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- Facile synthesis of α-amino phosphonates in water by Kabachnik-Fields reaction using magnesium dodecyl sulfate
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The three-component reaction of aldehydes, amines and triethyl or diphenyl phosphite was efficiently catalyzed by magnesium dodecyl sulfate at room temperature in water to give various α-amino phosphonates in high yields. The catalyst is easily available from inexpensive sodium dodecyl sulfate and magnesium bromide.
- Ando, Kaori,Egami, Tomoe
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experimental part
p. 358 - 362
(2012/01/06)
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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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- CeCl37H2O-catalyzed one-pot Kabachnik-Fields reaction: A green protocol for three-component synthesis of α- aminophosphonates
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CeCl37H2O has been utilized as an efficient Lewis acid catalyst for the three-component coupling of aldehydes, aromatic amines, and diethylphosphite to produce α-aminophosphonates under solvent-free conditions. The advantages of this protocol are high yield, mild reaction conditions, less environmental pollution, and simple work-up procedure.
- Jafari, Abbas Ali,Nazarpour, Mahshid,Abdollahi-Alibeik, Mohammad
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experimental part
p. 397 - 403
(2011/07/07)
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- Silica gel and polystyrene supported aluminum chloride as heterogeneous catalysts for the preparation of α-aminophosphonates
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Silica gel supported aluminum chloride (SiO2-AlCl3) and cross-linked polystyrene-supported aluminum chloride (PS-AlCl3) are environment- friendly heterogeneous catalysts for the condensation of amines and aldehydes with diethyl phosphite to afford α-aminophosphonates. These solid acid catalysts are stable (as bench top catalysts) and can be easily recovered and reused without appreciable change in their efficiency.
- Boroujeni, Kaveh Parvanak,Shirazi, Amir Nasrolahi
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experimental part
p. 418 - 422
(2011/06/28)
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- Solvent-free sonochemical preparation of α-aminophosphonates catalyzed by 1-hexanesulphonic acid sodium salt
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1-Hexanesulphonic acid sodium salt was found to be an efficient catalyst for the green synthesis of α-aminophosphonates by the coupling of aldehydes/ketone, an amine and triethyl phosphite under ultrasound irradiation at ambient temperature for appropriate time to furnish the desired product in good to excellent yield under solvent-free condition. This catalyst provides clean conversion; greater selectivity and easy workup make this protocol practical and economically attractive.
- Niralwad, Kirti S.,Shingate, Bapurao B.,Shingare, Murlidhar S.
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experimental part
p. 760 - 763
(2011/10/08)
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- Micellar solution of sodium dodecyl sulfate (SDS) catalyzes Kabacknik-Fields reaction in aqueous media
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A new, convenient and high-yielding procedure for the one-pot synthesis of diethyl α-aminophosphonates from aldehydes, amines and diethyl phosphite (Kabacknik-Fields reaction) in SDS micellar solution in aqueous media is described. The synthesis of aaminophosphonates in the present study represents a three-component reaction in which no intermediate formation of either an imine or α-hydroxyphosphonate was observed. Georg Thieme Verlag Stuttgart.
- Sobhani, Sara,Vafaee, Asieh
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experimental part
p. 1909 - 1915
(2009/12/30)
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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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- An eco-friendly procedure for the efficient synthesis of dialkyl α-aminophosphonates in aqueous media
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A new, convenient and high yielding procedure for the preparation of diethyl α-aminophosphonates in water by one-pot reaction of aldehydes, amines, tri/dialkyl phosphites in the presence of a low catalytic amount of [Cu(3,4-tmtppa)](MeSO4)4 (0.16 mol%) as a highly stable and re-usable catalyst is described.
- Sobhani, Sara,Safaei, Elham,Asadi, Mozaffar,Jalili, Fariba
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p. 3313 - 3317
(2008/12/22)
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- Facile one-pot synthesis of α-amino phosphonates using lanthanide chloride as catalyst
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An efficient preparation of α-amino phosphonates by the one-pot condensation of aldehydes, amines, and dialkyl phosphites using catalytic amounts of lanthanide chloride under mild conditions is successfully developed. Moreover, the catalyst is water-tolerant and could be recovered and reused.
- Xu, Fan,Luo, Yiqin,Wu, Jianting,Shen, Qi,Chen, Hou
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p. 389 - 392
(2007/10/03)
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