CuFe2O4 nanoparticles: A magnetically recoverable and reusable catalyst for the synthesis of coumarins via pechmann reaction in water

Synthetic Communications

Volumn 44, Issue 5, 2014, Pages 697-706

  Baghbanian, Seyed Meysam ^a   Farhang, Maryam ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

Coumarins; CuFe2O4 nanoparticles; heterogeneous catalyst; Pechmann reaction

Indexed keywords

3 AMINOPHENOL; ACETOACETIC ACID DERIVATIVE; COPPER; COUMARIN DERIVATIVE; FERRITE; MAGNETIC NANOPARTICLE; PHENOL DERIVATIVE; RESORCINOL; WATER;

ARTICLE; CHEMICAL REACTION; NANOCATALYST; PECHMANN REACTION; RECYCLING; ROOM TEMPERATURE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 84891551731     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.835423     Document Type: Article

References (32)

1. Chikazumi, S.; Taketomi, S.; Ukita, M.; Mizukami, M.; Miyajima, H.; Setogawa, M.; Kurihara, Y. Physics of magnetic fluids. J. Magn. Magn. Mater. 1987, 65, 245-251
2. Lu, A. H.; Schmidt, W.; Matoussevitch, N.; Pnnermann, H.; Spliethoff, B.; Tesche, B.; Bill, E.; Kiefer, W.; Schü th, F. Nanoengineering of a magnetically separable hydrogenation catalyst. Angew. Chem. 2004, 116, 4403-4410
3. Hyeon, T. Chemical synthesis of magnetic nanoparticles. Chem. Commun. 2003, 927-934
4. Elliott, D. W.; Zhang, W. X. Field assessment of nanoscale bimetallic particles for groundwater treatment. Environ. Sci. Technol. 2001, 35, 4922-4926
5. Weber, U. S.; Steffen, B.; Siegers, C. P. Antitumor activities of coumarin, 7-hydroxycoumarin, and its glucuronide in several human tumor cell lines. Res. Commun. Mol. Pathol. Pharmacol. 1998, 99, 193-206
6. Patil, A. D.; Freyer, A. J.; Drake, S. E.; Haltiwanger, R. C.; Bean, M. F.; Taylor, P. B.; Caranfa, M. J.; Breen, A. L.; Bartus, H. R.; Johnson, R. K.; Hertzberg, R. P.; Westley, J. W. The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn. J. Med. Chem. 1993, 36, 4131-4138
7. Yun, B. S.; Lee, I. K.; Ryoo, I. J.; Yoo, I. D. Coumarins with monoamine oxidase inhibitory activity and antioxidative coumarino-lignans from Hibiscus syriacus. J. Nat. Prod. 2001, 64, 1238-1240
8. Zaha, A. A.; Hazem, A. Antimicrobial activity of two novel coumarin derivatives: 3-Cyanonaphtho[1,2-(e)] pyran-2-one and 3-cyanocoumarin. New Microbiol. 2002, 25, 213-222
9. Maly, D. J.; Leonetti, F.; Backes, B. J.; Dauber, D. S.; Harris, J. L.; Craik, C. S.; Ellman, J. A. Expedient solid-phase synthesis of fluorogenic protease substrates using the 7-amino-4 carbamoylmethylcoumarin (ACC) fluorophore. J. Org. Chem. 2002, 67, 910-915
10. Kennedy, R. O.; Thornes, R. D. Coumarins: Biology, Applications, and Mode of Action; John Wiley and Sons, Chichester, 1997
11. Sabou, R.; Hoelderich, W. F.; Ramprasad, D.; Weinand, R. J. Synthesis of 7-hydroxy-4-methylcoumarin via the Pechmann reaction with Amberlyst ion-exchange resins as catalysts. J. Catal. 2005, 232, 34-37
12. Li, T. S.; Zhang, Z. H.; Yang, F.; Fu, C. G. Montmorillonite clay catalysis, part 7: An environmentally friendly procedure for the synthesis of coumarins via Pechmann condensation of phenols with ethyl acetoacetate. J. Chem. Res. Synop. 1998, 38-39
13. Laufer, M. C.; Hausmann, H.; Holherich, W. F. Synthesis of 7-hydroxycoumarins by Pechmann reaction using Nafion resin=silica nanocomposites as catalysts. J. Catal. 2003, 218, 315-320
14. Tyagi, B.; Mishra, M. K.; Jasra, R. V. Synthesis of 7-substituted 4-methyl coumarins by Pechmann reaction using nano-crystalline sulfated-zirconia. J. Mol. Catal. A: Chem. 2007, 276, 47-56
15. Pechmann, V. H. Neue Bildungsweise der Cumarine: Synthese des Daphnetins, I. Chem. Ber. 1884, 17, 929-936
16. Woods, L. L.; Sapp, J. A new one-step synthesis of substituted coumarins. J. Org. Chem. 1962, 27, 3703-3705
17. Robertson, A.; Sandrock, W. F.; Henry, C. B. Hydroxy-carbonyl compounds, part V: The preparation of coumarins and 1:4-pyrones from phenol, p-cresol, quinol, and a-naphthol. J. Chem. Soc. 1931, 2426-2432
18. Karimi, B.; Zareyee, D. Design of a highly efficient and water-tolerant sulfonic acid nanoreactor based on tunable ordered porous silica for the von Pechmann reaction. Org. Lett. 2008, 18, 3989-3992
19. Sharma, G. V. M.; Janardhan, R. J.; Sree, L. P.; Radha, K. P. An efficient ZrCl4-catalyzed, one-pot, solvent-free protocol for the synthesis of 4-substituted coumarins. Tetrahedron Lett. 2005, 46, 6119-6121
20. Valizadeh, H.; Shockravi, A. An efficient procedure for the synthesis of coumarin derivatives using TiCl4 as catalyst under solvent-free conditions. Tetrahedron Lett. 2005, 46, 3501-3503
21. Nedkov, I.; Vandenberghe, R. E.; Marinova, T.; Thailhades, P.; Merodiiska, T.; Avramova, I. Magnetic structure and collective Jahn-Teller distortions in nanostructured particles of CuFe2O4. Appl. Surf. Sci. 2006, 253, 2589-2596
22. Varughese, M. A.; Ramakrishna, P. B.; Shriniwas, D. S. Bismuth(III) nitrate pentahydrate, a mild and inexpensive reagent for synthesis of coumarins under mild conditions. Tetrahedron Lett. 2005, 46, 6957-6959
23. Bahekar, S. S.; Shinde, D. B. Samarium(III)-catalyzed one-pot construction of coumarins. Tetrahedron Lett. 2004, 45, 7999-8001
24. Hegedü s, A.; Hell, Z. Zeolite-catalyzed Pechmann synthesis of coumarins. Catal. Lett. 2006, 112, 105-108
25. Karimi, B.; Behzadnia, H. Periodic mesoporous silica chloride (PMSCl) as an efficient and recyclable catalyst for the Pechmann reaction. Catal. Commun. 2011, 12, 1432-1436
26. Sharma, R. K.; Monga, Y.; Puri A. Zirconium(IV)-modified silica@magnetic nanocomposites: Fabrication, characterization, and application as efficient, selective, and reusable nanocatalysts for Friedel-Crafts, Knoevenagel, and Pechmann condensation reactions. Catal. Commun. 2013, 35, 110-114
27. Karami, B.; Kiani, M. ZrOCl2 8H2O=SiO2: An efficient and recyclable catalyst for the preparation of coumarin derivatives by Pechmann condensation reaction. Catal. Commun. 2011, 14, 62-67
28. Sharma, R. K.; Sharma, C. Zirconium(IV)-modified silica gel: Preparation, characterization, and catalytic activity in the synthesis of some biologically important molecules. Catal. Commun. 2011, 12, 327-331
29. Reddy, Y.; Sonar, N.; Crooks, A.; Dasari, K.; Reddy, P.; Rajitha, B. Ceric ammonium nitrate (CAN): An efficient catalyst for the coumarin synthesis via Pechmann condensation using conventional heating and microwave irradiation. Synth. Commun. 2008, 38, 2082-2088
30. Peipei, S.; Zhixin, H. FeCl3-catalyzed Pechmann synthesis of coumarins in ionic liquids. Synth. Commun. 2008, 38, 2646-2654
31. Subhas Bose, D.; Rudradas, A. P.; Hari Babu, M. The indium(III) chloride-catalyzed von Pechmann reaction: A simple and effective procedure for the synthesis of 4-substituted coumarins. Tetrahedron Lett. 2002, 43, 9195-9197
32. Smitha, G.; Reddy, C. S. ZrCl4-catalyzed Pechmann reaction: Synthesis of coumarins under solvent-free conditions. Synth. Commun. 2004, 34, 3997-4003