Nano-TiO2 catalyzed microwave synthesis of α-Hydroxyphosphonates

Organic Communications

Volumn 7, Issue 3, 2014, Pages 98-105

  Prasad, S Siva ^a   Jayaprakash, S H ^a   Rao, K Umamaheswara ^a   Reddy, N Bakthavatchala ^a   Rohini Kumar, P Chenna ^a   Reddy, C Suresh ^a  

^a SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

Hydro phosphonylation; Microwave; Nano TiO2; Hydroxyphosphonates

Indexed keywords

EID: 84930189706     PISSN: None     EISSN: 13076175     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Westheimer, F. H. Why Nature Chose Phosphates. Science, 1987, 235, 1173-1178.
2. Uhlmann, E.; Peyman, A. Antisense oligonucleotides: a new therapeutic principle. Chem. Rev. 1990, 90, 543-584.
3. Hélène, C. The anti-gene strategy: control of gene expression by triplex-formingoligonucleotides. Anticancer Drug Des. 1991, 6, 569-584.
4. Nawrot, B.; Sipa, K. Chemical and Structural Diversity of siRNA Molecules. Curr. Top. Med. Chem. 2006, 6, 913-925.
5. Subba Reddy, S.; Koteswara Rao, V.; Satheesh Krishna, B.; Suresh Reddy, C.; Visweswara Rao, P.; Naga Raju, C. Synthesis, Antimicrobial, and Antioxidant Activity of New α-Aminophosphonates. Phosphorus, Sulfur, and Silicon, 2011, 186, 1411-1421.
6. Olah, G. A.; Wu, A. Synthetic methods and reactions. 159. Preparation of 1,2-diketones from nonenolizable aliphatic and aromatic acyl chlorides with diethyl 1-alkyl(aryl)-1-(trimethylsiloxy)-methanephosphonates. J. Org. Chem. 1991, 56, 902-904.
7. Iorga, B.; Eymery, F.; Savignac, P. Controlled monohalogenation of phosphonates: A new route to pure α-monohalogenated diethyl benzylphosphonates. Tetrahedron, 1999, 55, 2671-2686.
8. Neyts, J.; De Clercq, E. Antiviral Drug Susceptibility of Human Herpesvirus 8. Antimicrob. Agents Chemother. 1997, 41, 2754-2756.
9. Fleisch, H. Bisphosphonates: Mechanisms of Action. Endocrine Rev. 1998, 19, 80-100.
10. Lee, M. V.; Fong, E. M.; Singer, F. R.; Guenett, R. S. Bisphosphonate Treatment Inhibits the Growth of Prostate Cancer Cells. Cancer Res. 2001, 61, 2602-2608.
11. Uma Maheswara Rao, K.; Syama Sundar, Ch.; Siva Prasad, S.; Radha Rani, C.; Suresh Reddy, C. Neat Synthesis and Anti-oxidant Activity of α-hydroxyphosphonates. Bull. Korean Chem. Soc. 2011, 32, 3343-3347.
12. Pompliano, D. L.; Rands, E.; Schaber, M. D.; Mosser, S. D.; Anthony, N. J.; Gibbs, J. B. Steady-state kinetic mechanism of ras farnesyl:protein transferase. Biochemistry, 1992, 31, 3800-3807.
13. Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. Novel Peptidyl Phosphorus Derivatives as Inhibitors of Human Calpain I. J. Med. Chem. 1998, 41, 3912-3916.
14. Murano, T.; Yuasa, Y.; Kobayakawa, H.; Yokomatsu, T.; Shibuya, S. Synthesis of acyclic nucleotide analogues possessing a difluoromethylene phosphonyl group at the side chain. Tetrahedron, 2003, 59, 10223-10230.
15. Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Synthesis of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids and the related methano analogues. Remarkable effect of the nucleobases and the cyclopropane rings on inhibitory activity toward purine nucleoside phosphorylase. Bioorg. Med. Chem. 1998, 6, 2495-2505.
16. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han, C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. EPSP Synthase: The Design and Synthesis of Bisubstrate Inhibitors Incorporating Novel 3-Phosphate Mimics. Phosphorus Sulfur Silicon Relat. Elem. 1993, 76, 115-118.
17. Kafarski, P.; Lejczak, B. Application of bacteria and fungi as biocatalysts for the preparation of optically active hydroxyphosphonates. J. Mol. Catal. B: Enzym. 2004, 29, 99-104.
18. Wynberg, H.; Smaardijk, A. A. Asymmetric catalysis in carbon-phosphorus bond formation. Tetrahedron Lett. 1983, 24, 5899-5990.
19. Akiyamam, T.; Morita, H.; Itoh, J.; Fuchibe, K. Chiral Brønsted Acid Catalyzed Enantioselective Hydrophosphonylation of Imines: Asymmetric Synthesis of α-Amino Phosphonates. Org. Lett. 2005, 7, 2583-2585.
20. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. New homochiral cyclic diol ligands for titanium alkoxide catalyzed phosphonylation of aldehydes. Tetrahedron Lett. 1998, 39, 5485-5488.
21. Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. Catalytic Asymmetric Synthesis of α-Hydroxy Phosphonates Using the Al-Li-BINOL Complex. J. Org. Chem. 1996, 61, 2926-2927.
22. Texier-Boullet, F.; Lequitte, M. An unexpected reactivity of simple heterogeneous mixture of γ-alumina and potassium fluoride: 1-hydroxyalkane phosphonic esters synthesis from non-activated ketones in "dry media". Tetrahedron Lett. 1986, 27, 3515-3516.
23. Swapnil, S. S.; Amol, H. K.; Madhav, N. W.; Charansingh, H. G.; Bapurao, B. S.; Murlidhar, S. S. Ammonium metavanadate: an effective catalyst for synthesis of α-hydroxyphosphonates. Arkivoc, 2009, ii, 138-148.
24. Simoni, D.; Rondanin, R.; Morini, M.; Baruchello, R.; Lnvidiata, F. P. 1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems. Tetrahedron Lett. 2000, 41, 1607-1610.
25. Shen, L.; Liu, R.; Liao, X.; Ye, Y. Green synthesis of a-hydroxyl phosphate under solvent-free condition. Huaxue Yanjiu Yu Yingyong. 2010, 21, 40-43.
26. Keglevich, G.; Toth, V. R.; Drahos, L. Microwave-assisted synthesis of a-hydroxy-benzylphosphonates and -benzylphosphine oxides. Heteroatom Chem. 2011, 22, 15-17.
27. Sun, J. Y.; Wang, J. X.; Pei, Q.; Jin, C. X.; Zhang, X. N. The synthesis of a-hydroxy phosphonate compounds without solvents. Xinyang Shifan Xueyuan Xuebao. 2009, 22, 588-589.
28. Mandhane, P. G.; Joshi, R. S.; Nagargoje, D. R.; Gill, C. H. Ultrasound-promoted greener approach to synthesize a-hydroxy phosphonates catalyzed by potassium dihydrogen phosphate under solvent-free condition. Tetrahedron Lett. 2010, 51, 1490-1492.
29. Wang, H. S.; Zeng, J. E. Iodine-catalyzed, efficient synthesis of a-hydroxy phosphonates in water. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 1425-1428.
30. Richards, R.; Li, W.; Decker, S.; Davidson, C.; Koper, O.; Zaikovski, V.; Volodin, A.; Rieker, T. Consolidation of Metal Oxide Nanocrystals. Reactive Pellets with Controllable Pore Structure That Represent a New Family of Porous, Inorganic Materials. J. Am. Chem. Soc, 2000, 122, 4921-4925.
31. 2 nanopowder. Tetrahedron Lett. 2013, 54, 1371-1379.
32. Sarkar, R.; Mukhopadhyay, C. Admicellar catalysis in multicomponent synthesis of polysubstituted pyrrolidinones. Tetrahedron Lett, 2013, 54, 3706-3711.
33. Wang, J.; Sun, W.; Zhang, Z.; Zhang, X.; Li, R.; Ma, T.; Zhang, P.; Li, Y. Sonocatalytic degradation of methyl parathion in the presence of micron-sized and nano-sized rutile titanium dioxide catalysts and comparison of their sonocatalytic abilities. J. Mol. Catal. A: Chem. 2007, 272, 84-90.
34. 2 Based Catalysts for Rhodamine B Degradation. Turk. J. Chem. 2007, 31, 211-221.
35. 2 catalyst. Polymer, 2006, 47, 8155-8162.
36. Rajalakshmi, N.; Lakshmi, N.; Dhathathreyan, K. S. Nano titanium oxide catalyst support for proton exchange membrane fuel cells. Inter. J. Hydrogen Energy, 2008, 33, 7521-7526.
37. 2 As Co-Catalyst for Improving Wrinkle-Resistance of Cotton Fabric. Surf. Rev. Lett. 2007, 14, 571-575.
38. 2/Ag catalyst. React. Kinet. Catal. Lett. 2007, 90, 267-273.
39. Chen, C.-C.; Wang, C.-C. Crosslinking of cotton cellulose with succinic acid in the presence of titanium dioxide nano-catalyst under UV irradiation. J Sol-Gel Sci Techn. 2006, 40, 31-38.
40. Sardarian, A. R.; Kaboudin, B. Surface-Mediated Solid Phase Reactions: Preparation of Diethyl 1-Hydroxyarylmethylphosphonates on the Surface of Magnesia. Synthetic Comm. 1997, 27, 543-551.