Main Article Content
Abstract
To achieve an efficient synthesis of some novel α-aminophosphonates via Pudovik reaction; ultrasonic irradiation has been adopted. Major benefits of this method is eco-friendly, free of catalyst, high yielding, uncomplicated work-up procedure, short reaction time and solvent free condition. Spectral characterization and elemental analysis of the synthesized samples was carried out. In vitro antioxidant activity of the synthesized a-aminophosphonates compounds was screened by DPPH•, O2•− and NO• scavenging methods. Good to moderate activities were shown by most of the compounds while compared with the standards.
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Copyright (c) 2018 Asian Journal of Organic & Medicinal Chemistry

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References
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- M.Z. Kassaee, F. Movaheddi and H. Masrouri, ZnO Nanoparticles as an Efficient Catalyst for the One-Pot Synthesis of a-Amino Phosphonates, Synlett., 1330 (2009); https://doi.org/10.1055/s-0028-1088135
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- K.S. Ambica, S.C. Taneja, M.S. Hundal and K.K. Kapoor, One-Pot Synthesis of a-aminophosphonates Catalyzed by Antimony Trichloride Adsorbed on Alumina, Tetrahedron Lett., 49, 2208 (2008); https://doi.org/10.1016/j.tetlet.2008.02.047
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- S. Sobhani, E. Safaei, M. Asadi and F. Jalili, An Eco-friendly Procedure for the Efficient Synthesis of Dialkyl a-aminophosphonates in Aqueous Media, J. Organomet. Chem., 693, 3313 (2008); https://doi.org/10.1016/j.jorganchem.2008.07.037
- P. Anastas and N. Eghbali, Green Chemistry: Principles and Practice, Chem. Soc. Rev., 39, 301 (2010); https://doi.org/10.1039/B918763B
- Y.B. Huang, M. Shen, X. Wang, P. Huang, R. Chen, Z.J. Lin and R. Cao, Water-Medium C–H Activation Over a Hydrophobic Perfluoro Alkane-Decorated Metal-Organic Framework Platform, J. Catal., 333, 1 (2016); https://doi.org/10.1016/j.jcat.2015.10.012
- R. Juarez, P. Concepcion, A. Corma and H. Garcia, Ceria Nanoparticles as Heterogeneous Catalyst for CO2 Fixation by w-Aminoalcohols, Chem. Commun. 46, 4181 (2010); https://doi.org/10.1039/c001955k
- R. Juarez, A. Corma and H. Garcia, Gold Nanoparticles Promote the Catalytic Activity of Ceria for the Transalkylation of Propylene Carbonate to Dimethyl Carbonate, Green Chem., 11, 949 (2009); https://doi.org/10.1039/b902850a
- R. Gallardo-Macias and K. Nakayama, Tin(II) Compounds as Catalysts for the Kabachnik-Fields Reaction under Solvent-Free Conditions: Facile Synthesis of a-Aminophosphonates, Synthesis, 57 (2010); https://doi.org/10.1055/s-0029-1217091
- A. Heydari, H. Hamadi and M. Pourayoubi, A New One-Pot Synthesis of a-Amino Phosphonates Catalyzed by H3PW12O40, Catal. Commun., 8, 1224 (2007); https://doi.org/10.1016/j.catcom.2006.11.008
- P.V. Shinde, A.H. Kategaonkar, B.B. Shingate and M.S. Shingare, An Organocatalyzed Facile and Rapid Access to a-Hydroxy and a-Amino Phosphonates under Conventional/Ultrasound Technique, Tetrahedron Lett., 52, 2889 (2011); https://doi.org/10.1016/j.tetlet.2011.03.138
- S.M. Agawane and J.M. Nagarkar, Nano Ceria Catalyzed Synthesis of a-Aminophosphonates under Ultrasonication, Tetrahedron Lett., 52, 3499 (2011); https://doi.org/10.1016/j.tetlet.2011.04.112
- D. Ravikumar, S. Mohan, C. Subramanyam and K.P. Rao, Solvent-Free Sonochemical Kabachnic Fields Reaction to Synthesize Some New a-Aminophosphonates Catalyzed by Nano-BF3·SiO2, Phosphorus, Sulfur, Silicon Rel. Elem., 193, 400 (2018); https://doi.org/10.1080/10426507.2018.1424163
- N. Cotelle, J.L. Bemier, J.P. Catteau, J. Pommery, J.C. Wallet and E.M. Gaydou, Antioxidant Properties of Hydroxy-Flavones, Free Radic. Biol. Med., 20, 35 (1996); https://doi.org/10.1016/0891-5849(95)02014-4
- J. Robak and R.J. Gryglewski, Flavonoids are Scavengers of Superoxide Anions, Biochem. Pharmacol., 37, 837 (1988); https://doi.org/10.1016/0006-2952(88)90169-4
- L.C. Green, D.A. Wagner, J. Glogowski, P.L. Skipper, J.S. Wishnok and S.R. Tannenbaum, Analysis of Nitrate, Nitrite and Nitrate in Biological Fluids, Anal. Biochem., 126, 131 (1982); https://doi.org/10.1016/0003-2697(82)90118-x
- L. Marcocci, L. Packer, M. T. Droy-Lefaix, A. Sekaki and M. Gardès-Albert. Antioxidant action of Ginkgo biloba extracts EGB 761, Methods Enzymol., 234, 462 (1994); https://doi.org/10.1016/0076-6879(94)34117-6
References
P. Merino, E. Marqués-López, R. P. Herrera, Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines. Adv. Synth. Catal., 350, 1195 (2008); https://doi.org/10.1002/adsc.200800131
K. Moonen, I. Laureyn and C.V. Stevens, Synthetic Methods for Azaheterocyclic Phosphonates and their Biological Activity, Chem. Rev., 104, 6177 (2004); https://doi.org/10.1021/cr030451c
F. Palacios, C. Alonso, & J. M. de los Santos, a-Phosphono and Phosphino Peptides derived from a-Aminophosphonic and Phosphinic Acids, Curr. Org. Chem., 8, 1481 (2004); https://doi.org/10.2174/1385272043369863
K.A. Schug and W. Lindner, Noncovalent Binding Between Guanidinium and Anionic Groups: Focus on Biological and Synthetic-based Arginine/Guanidinium Interactions with Phosphonate and Sulfonate Residues, Chem Rev., 105, 67 (2005); https://doi.org/10.1021/cr040603j
C. Subramanyam, S.K. Taslim Bhasha, G. Madhava, S.K. Adam, S.D. Srinivasa Murthy and C.N. Raju, Synthesis, Spectral Characterization and Bioactivity Evaluation of Novel a-Aminophosphonates, Phosphorus, Sulfur, Silicon Rel. Elem., 192, 267 (2017); https://doi.org/10.1080/10426507.2016.1225056
S. Yang, X.W. Gao, & C. L. Diao, Synthesis and Antifungal Activity of Novel Chiral a-Aminophosphonates Containing Fluorine Moiety, Chin. J. Chem., 24, 11, 1581 (2006); https://doi.org/10.1002/cjoc.200690296
Y. Xu, K. Yan, B. Song, G. Xu, S. Yang, W. Xue, D. Hu, P. Lu, G. Ouyang, L. Jin and Z. Chen,, Synthesis and Antiviral Bioactivities of a-Aminophosphonates containing Alkoxyethyl Moieties, Molecules, 11, 666 (2006); https://doi.org/10.3390/11090666
B. Sujatha, S. Mohan, C. Subramanyam and K.P. Rao, Microwave-Assisted Synthesis and Anti-inflammatory Activity Evaluation of Some Novel a-aminophosphonates, Phosphorus, Sulfur, Silicon Rel. Elem., 192, 1110 (2017); https://doi.org/10.1080/10426507.2017.1331233
I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lutzen and J. Martens, Diastereoselective Lewis Acid Mediated Hydrophosphony-lation of Heterocyclic Imines: A Stereoselective Approach towards a-Aminophosphonates, J. Chem. Soc. Perkin Trans. I, 2804 (2001); https://doi.org/10.1039/B101501J
A. Manjula, B.V. Rao and P. Neelakantan, One-Pot Synthesis of a-Aminophosphonates: An Inexpensive Approach, Synth. Commun. 33, 2963 (2013); https://doi.org/10.1081/SCC-120022468
J.S. Yadav, B.V.S. Reddy, K.S. Raj, K.B. Reddy and A.R. Prasad, ZrCl4-Catalyzed Efficient Synthesis of a-Aminophosphonates, Synthesis, 2277 (2001); https://doi.org/10.1055/s-2001-18444
N. Azizi, F. Rajabi and M.R. Saidi, A Mild and Highly Efficient Protocol for the One-Pot Synthesis of Primary a-Amino Phosphonates under Solvent-Free Conditions, Tetrahedron Lett., 45, 9233 (2004); https://doi.org/10.1016/j.tetlet.2004.10.092
M.Z. Kassaee, F. Movaheddi and H. Masrouri, ZnO Nanoparticles as an Efficient Catalyst for the One-Pot Synthesis of a-Amino Phosphonates, Synlett., 1330 (2009); https://doi.org/10.1055/s-0028-1088135
A. Heydari, A. Karimian and J. Ipaktschi, Lithium Perchlorate/Diethyl-ether Catalyzed Aminophosphonation of Aldehydes, Tetrahedron Lett., 39, 6729 (1998); https://doi.org/10.1016/S0040-4039(98)01411-7
S. Chandrasekhar, S.J. Prakash, V. Jagadeshwar and C. Narsihmulu, Three Component Coupling Catalyzed by TaCl5-SiO2: Synthesis of a-Amino Phosphonates, Tetrahedron Lett., 42, 5561 (2001); https://doi.org/10.1016/S0040-4039(01)01053-X
J.S. Yadav, B.V.S. Reddy and P. Sreedhar, Three Component One Pot Synthesis of a-Hydroxylamino Phosphonates using Ionic Liquids, Adv. Synth. Catal., 345, 564 (2003); https://doi.org/10.1002/adsc.200202209
A.K. Bhattacharya and T. Kaur, An Efficient One-Pot Synthesis of a-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate, Synlett, 745 (2007); https://doi.org/10.1055/s-2007-970762
A. Heydari, H. Hamadi and M. Pourayoubi, A New One-pot Synthesis of a-Aminophosphonates Catalyzed by H3PW12O40, Catal. Commun. 8, 1224 (2007); https://doi.org/10.1016/j.catcom.2006.11.008
S.D. Mitragotri, D.M. Pore, U.V. Desai and P.P. Wadgaonkar, Sulfamic Acid: An Efficient and Cost-Effective Solid Acid Catalyst for the Synthesis of a-Aminophosphonates at Ambient Temperature, Catal. Commun., 9, 1822 (2008); https://doi.org/10.1016/j.catcom.2008.02.011
S.M. Vahdat, R. Baharfar, M. Tajbakhsh, A. Heydari, S.M. Baghbanian and S. Khaksar, Organocatalytic Synthesis of a-Hydroxy and a-Aminophosphonates, Tetrahedron Lett. 49, 6501 (2008); https://doi.org/10.1016/j.tetlet.2008.08.094
K.S. Ambica, S.C. Taneja, M.S. Hundal and K.K. Kapoor, One-Pot Synthesis of a-aminophosphonates Catalyzed by Antimony Trichloride Adsorbed on Alumina, Tetrahedron Lett., 49, 2208 (2008); https://doi.org/10.1016/j.tetlet.2008.02.047
A.K. Bhattacharya and K.C. Rana, Amberlite-IR 120 Catalyzed Three-Component Synthesis of A-aminophosphonates in One-Pot, Tetrahedron Lett., 49, 2598 (2008); https://doi.org/10.1016/j.tetlet.2008.02.102
S. Sobhani, E. Safaei, M. Asadi and F. Jalili, An Eco-friendly Procedure for the Efficient Synthesis of Dialkyl a-aminophosphonates in Aqueous Media, J. Organomet. Chem., 693, 3313 (2008); https://doi.org/10.1016/j.jorganchem.2008.07.037
P. Anastas and N. Eghbali, Green Chemistry: Principles and Practice, Chem. Soc. Rev., 39, 301 (2010); https://doi.org/10.1039/B918763B
Y.B. Huang, M. Shen, X. Wang, P. Huang, R. Chen, Z.J. Lin and R. Cao, Water-Medium C–H Activation Over a Hydrophobic Perfluoro Alkane-Decorated Metal-Organic Framework Platform, J. Catal., 333, 1 (2016); https://doi.org/10.1016/j.jcat.2015.10.012
R. Juarez, P. Concepcion, A. Corma and H. Garcia, Ceria Nanoparticles as Heterogeneous Catalyst for CO2 Fixation by w-Aminoalcohols, Chem. Commun. 46, 4181 (2010); https://doi.org/10.1039/c001955k
R. Juarez, A. Corma and H. Garcia, Gold Nanoparticles Promote the Catalytic Activity of Ceria for the Transalkylation of Propylene Carbonate to Dimethyl Carbonate, Green Chem., 11, 949 (2009); https://doi.org/10.1039/b902850a
R. Gallardo-Macias and K. Nakayama, Tin(II) Compounds as Catalysts for the Kabachnik-Fields Reaction under Solvent-Free Conditions: Facile Synthesis of a-Aminophosphonates, Synthesis, 57 (2010); https://doi.org/10.1055/s-0029-1217091
A. Heydari, H. Hamadi and M. Pourayoubi, A New One-Pot Synthesis of a-Amino Phosphonates Catalyzed by H3PW12O40, Catal. Commun., 8, 1224 (2007); https://doi.org/10.1016/j.catcom.2006.11.008
P.V. Shinde, A.H. Kategaonkar, B.B. Shingate and M.S. Shingare, An Organocatalyzed Facile and Rapid Access to a-Hydroxy and a-Amino Phosphonates under Conventional/Ultrasound Technique, Tetrahedron Lett., 52, 2889 (2011); https://doi.org/10.1016/j.tetlet.2011.03.138
S.M. Agawane and J.M. Nagarkar, Nano Ceria Catalyzed Synthesis of a-Aminophosphonates under Ultrasonication, Tetrahedron Lett., 52, 3499 (2011); https://doi.org/10.1016/j.tetlet.2011.04.112
D. Ravikumar, S. Mohan, C. Subramanyam and K.P. Rao, Solvent-Free Sonochemical Kabachnic Fields Reaction to Synthesize Some New a-Aminophosphonates Catalyzed by Nano-BF3·SiO2, Phosphorus, Sulfur, Silicon Rel. Elem., 193, 400 (2018); https://doi.org/10.1080/10426507.2018.1424163
N. Cotelle, J.L. Bemier, J.P. Catteau, J. Pommery, J.C. Wallet and E.M. Gaydou, Antioxidant Properties of Hydroxy-Flavones, Free Radic. Biol. Med., 20, 35 (1996); https://doi.org/10.1016/0891-5849(95)02014-4
J. Robak and R.J. Gryglewski, Flavonoids are Scavengers of Superoxide Anions, Biochem. Pharmacol., 37, 837 (1988); https://doi.org/10.1016/0006-2952(88)90169-4
L.C. Green, D.A. Wagner, J. Glogowski, P.L. Skipper, J.S. Wishnok and S.R. Tannenbaum, Analysis of Nitrate, Nitrite and Nitrate in Biological Fluids, Anal. Biochem., 126, 131 (1982); https://doi.org/10.1016/0003-2697(82)90118-x
L. Marcocci, L. Packer, M. T. Droy-Lefaix, A. Sekaki and M. Gardès-Albert. Antioxidant action of Ginkgo biloba extracts EGB 761, Methods Enzymol., 234, 462 (1994); https://doi.org/10.1016/0076-6879(94)34117-6