Introduction of W-doped ZnO nanocomposite as a new and efficient nanocatalyst for the synthesis of biscoumarins in water

Journal of Nanostructure in Chemistry

Volumn 5, Issue 1, 2015, Pages 123-130

  Shirini, Farhad ^a   Abedini, Masoumeh ^a   Zamani, Solmaz ^a   Fallah Moafi, Hadi ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

Aldehydes; Biscoumarins; Heterogeneous reaction conditions; Protected aldehydes; W doped ZnO nanocomposite

Indexed keywords

EID: 84963553055     PISSN: 20089244     EISSN: 21938865     Source Type: Journal    
DOI: 10.1007/s40097-014-0143-9     Document Type: Article

References (60)

1. Jung, J.C., Park, O.S.: Synthetic approaches and biological activities of 4-hydroxycoumarin derivatives. Molecules 14, 4790–4803 (2009) DOI: 10.3390/molecules14114790
2. Su, C.X., Mouscadet, J.F., Chiang, C.C., Tsai, H.J., Hsu, L.Y.: Integrase inhibition of biscoumarin analogues. Chem. Pharm. Bull. 54, 682–686 (2006) DOI: 10.1248/cpb.54.682
3. Kancheva, V.D., Boranova, V.P., Nechev, J., Manolov, I.I.: Structure-activity relationships of new 4-hydroxy bis-coumarins as radical scavengers and chain-breaking antioxidants. Biochimie 92, 1138–1146 (2010) DOI: 10.1016/j.biochi.2010.02.033
4. Khan, K.M., Iqbal, S., Lodhi, M.A., Maharvi, G.M., Ullah, Z., Choudhary, M.I., Rahman, A., Perveen, S.: Biscoumarin: new class of urease inhibitors; economical synthesis and activity. Bioorg. Med. Chem. 12, 1963–1968 (2004) DOI: 10.1016/j.bmc.2004.01.010
5. Kostova, I., Momekov, G., Zaharieva, M., Karaivanova, M.: Cytotoxic activity of new lanthanum (III complexes of bis-coumarins. Eur. J. Med. Chem. 40, 542–551 (2005) DOI: 10.1016/j.ejmech.2004.12.007
6. Gupta, A.D., Samanta, S., Mondal, R., Mallika, A.K.: A Convenient, eco-friendly, and efficient method for synthesis of 3,3′-arylmethylene-bis-4-hydroxycoumarins “on water”. Bull. Korean. Chem. Soc. 33, 4239–4242 (2012) DOI: 10.5012/bkcs.2012.33.12.4239
7. Karimi-Jaberi, Z., Nazarifar, M.R., Pooladian, B.: Tris(hydrogensulfato) boron as a solid heterogeneous catalyst for the rapid synthesis of α,α′-benzylidenebis(4-hydroxycoumarin) derivatives. Chin. Chem. Lett. 23, 781–784 (2012) DOI: 10.1016/j.cclet.2012.05.003
8. Padalkar, V., Phatangare, K., Takale, S., Pisal, R., Chaskar, A.: Silica supported sodium hydrogen sulfate and indion 190 resin: an efficient and heterogeneous catalyst for facile synthesis of bis-(4-hydroxycoumarin-3-yl)methanes. J. Saudi. Chem. Soc. (2012). doi:10.1016/j.jscs.2011.12.015
9. Khurana, J.M., Kumar, S.: Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions. Tetrahedron Lett. 50, 4125–4127 (2009) DOI: 10.1016/j.tetlet.2009.04.125
10. Heravi, M.M., Sadjadi, S., Mokhtari, H.N., Oskooie, H., Bamoharram, F.F.: Role of various heteropolyacids in the reaction of 4-hydroxycoumarin, aldehydes and ethylcyanoacetate. Catal. Commun. 10, 1643–1646 (2009) DOI: 10.1016/j.catcom.2009.04.031
11. Singh, P., Kumar, P., Katyal, A., Kalra, R., Dass, S.K., Prakash, S., Chandra, R.: Phosphotungstic acid: an efficient catalyst for the aqueous phase synthesis of bis-(4-hydroxycoumarin-3-yl)methanes. Catal. Lett. 134, 303–308 (2010) DOI: 10.1007/s10562-009-0239-x
12. Mehrabi, H., Abusaidi, H.: Synthesis of biscoumarin and 3,4-dihydro pyrano[c]chromene derivatives catalysed by sodium dodecyl sulfate (SDS) in neat water. J. Iran Chem. Soc. 7, 890–894 (2010) DOI: 10.1007/BF03246084
13. ParvanakBoroujeni, K., Ghasemi, P.: Synthesis and application of a novel strong and stable supported ionic liquid catalyst with both Lewis and Brønsted acid sites. Catal. Commun. 37, 50–54 (2013) DOI: 10.1016/j.catcom.2013.03.025
14. Shirini, F., Abedini, M., AbroonKiaroudi, S.: Introduction of titania sulfonic acid [TiO2–SO3H] as a new, efficient and reusable heterogenous solid acid catalyst for the synthesis of biscoumarins. Phosphorus Sulfur Silicon 189, 1279–1288 (2014) DOI: 10.1080/10426507.2013.858254
15. Greene, T.W., Wuts, P.G.M.: Protective Groups in Organic Synthesis, 3rd edn. Wiley, New York (1991)
16. Curini, M., Rostai, O., Pisani, E., Costantino U.: Heterogeneous catalysis in carbonyl regeneration from oximes, semicarbazones, and tosylhydrazones by zirconium sulphophenyl phosphonate. Synlett 4, 333–334 (1996) DOI: 10.1055/s-1996-5409
17. Kabalka, G.W., Pace, R.D., Wadgaonkar, P.P.,: Oximes from conjugated nitroalkenes using Pd/C-ammonium formate CTH. Synth. Commun. 20, 2453–2458 (19990)
18. Fujisawa, T., Kurita, Y., Sato, T.: A convenient synthesis of ketoximes from grignard reagents and nitro compounds activated by N,N-dimethyl chloromethyleniminium chloride. Chem. Lett. 10, 1537–1540 (1983) DOI: 10.1246/cl.1983.1537
19. Barton, D.H.R., Beaton, J.M., Geller, L.E., Pechet, M.M.,: A new photochemical reaction. J. Am. Chem. Soc. 83, 4076–4083 (1961)
20. Lee, K. Han, S.B., Yoo, E.M., Chung, S.R., Oh, H., Hong, S.: Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridinium iodide under mild conditions. Synth. Commun. 34, 1775–1782 (2004)
21. 3COCl: a new and highly efficient catalyst for dehydration of aldoximes into nitriles under solvent-free condition. Synthesis 5, 787–790 (2005)
22. Movassagh, B., Fazeli, A.: Direct synthesis of aromatic nitriles from aldehydes using hydroxylamine and oxalyl chloride. Synth. Commun. 37,623–628 (2007)
23. Schoenewalat, E.F., Kinnel, R.B., Davis, P.: Improved synthesis of anti-benzaldoxime. Concomitant cleavage and formylation of nitrones. J. Org. Chem. 33, 4270–4272 (1968) DOI: 10.1021/jo01275a059
24. Abiraj, K., Channe, G.D.: Zinc/ammonium formate: a new facile system for the rapid and selective reduction of oximes to amines. J. Chem. Res. (S) 6, 332–334 (2003) DOI: 10.3184/030823403103174281
25. 3 in the solid state. Synth. Commun. 28, 2275–2280 (1998) DOI: 10.1080/00397919808007044
26. Peter, W., Joan, M.F., Laura, S.: Microwave promoted oxazole synthesis: cyclocondensation cascade of oximes and acyl chlorides. Tetrahedron Lett. 46, 5463–5466 (2005) DOI: 10.1016/j.tetlet.2005.06.063
27. Hajipour, A.R., Mahboubghah, N.J.: 1-Benzyl-4-aza-1-azoniabicyclo [2.2.2]octaneperiodate: a mild and efficient oxidant for the cleavage of oxime double bonds under anhydrous conditions. J. Chem. Res. (S) 122–123 (1998)
28. A11 mechanism in the hydrolysis of benzylidenediacetates. J. Chem. Soc. B 1201–1207 (1970)
29. Heerden, F.R., Huyser, J.J., Williams, D.B.G., Holzapfer, C.W.: Palladium-catalysed substitution reactions of germinal allylicdiacetates. Tetrahedron Lett. 39, 5281–5284 (1998) DOI: 10.1016/S0040-4039(98)01000-4
30. Trost, B.M., Lee, C.: gem-Diacetates as carbonyl surrogates for asymmetric synthesis. Total syntheses of sphingofungins E and F. J. Am. Chem. Soc. 123, 12191–12201 (2001)
31. Sandberg, M. Sydnes, L.K.: The chemistry of acylals. Part II. Formation of nitriles by treatment of acylals with trimethylsilylazide in the presence of a Lewis acid. Tetrahedron. Lett. 39, 6361–6364 (1998)
32. Shirini, F., Abedini, M.: Application of nanocatalysts in multi-component reactions. J. Nanosci. Nanotech. 13, 4838–4860 (2013) DOI: 10.1166/jnn.2013.7571
33. Safaei-Ghomi, J., Ghasemzadeh, M.A.: Zinc oxide nanoparticles: A highly efficient and readily recyclable catalyst for the synthesis of xanthenes. Chin. Chem. Lett. 23, 1225–1229 (2012) DOI: 10.1016/j.cclet.2012.09.016
34. Maghsoodlou, M.T., Habibi-Khorassani, S.M., Shahkarami, Z., Maleki, N., Rostamizadeh, M.: An efficient synthesis of 2,2′-arylmethylene bis (3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 1,8-dioxo-octahydroxanthenes using ZnO and ZnO–acetyl chloride. Chin. Chem. Lett. 21, 686–689 (2010) DOI: 10.1016/j.cclet.2010.02.005
35. Tamaddon, F., Sabeti, M.R., Jafari, A.A., Tirgir, F., Keshavarz, E.: ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters. J. Mol. Catal. A Chem. 351, 41–45 (2011) DOI: 10.1016/j.molcata.2011.09.010
36. Paul, S., Bhattacharyya, P., Das, A.R.: One-pot synthesis of dihydropyrano[2,3-c]chromenes via a three component coupling of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin catalyzed by nano-structured ZnO in water: a green protocol. Tetrahedron Lett. 52, 4636–4641 (2011) DOI: 10.1016/j.tetlet.2011.06.101
37. Ghosh, P.P., Das, A.R.: Nano crystalline ZnO: a competent and reusable catalyst for one pot synthesis of novel benzylaminocoumarin derivatives in aqueous media. Tetrahedron Lett. 53, 3140–3143 (2012) DOI: 10.1016/j.tetlet.2012.04.033
38. Bhattacharyya, P., Pradhan, K., Paul, S., Das, A.R.: Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media. Tetrahedron Lett. 53, 4687–4691 (2012) DOI: 10.1016/j.tetlet.2012.06.086
39. Kassaee, M.Z., Movahedi, F., Masrouri, H.: ZnO nanoparticles as an efficient catalyst for the one-pot synthesis of α-amino phosphonates. Synlett 8, 1326–1330 (2009) DOI: 10.1055/s-0028-1088135
40. Dharma Rao, G.B., Kaushik, M.P., Halve, A.K.: An efficient synthesis of naphtha[1,2-e]oxazinone and 14-substituted-14H-dibenzo[a, j]xanthene derivatives promoted by zinc oxide nanoparticle under thermal and solvent-free conditions. Tetrahedron Lett. 53, 2741–2744 (2012) DOI: 10.1016/j.tetlet.2012.03.085
41. Kassaee, M.Z., Masrouri, H., Movahedi, F.: ZnO-nanoparticlepromoted synthesis of polyhydroquinoline derivatives via multicomponent Hantzsch reaction. Monatsh. Chem. 141, 317–322 (2010) DOI: 10.1007/s00706-010-0252-1
42. Sun, J.H., Dong, S.Y., Feng, J.L., Yin, X.J., Zhao, X.C.: Enhanced sunlight photocatalytic performance of Sn-doped ZnO for Methylene Blue degradation. J. Mol. Catal. A: Chem. 335, 145–150 (2011)
43. Patil, A.B., Patil, K.R., Pardeshi, S.K.: Ecofriendly synthesis and solar photocatalytic activity of S-doped ZnO. J. Hazard. Mater. 183, 315–323 (2010)
44. Wu, C., Shen, L., Yu, H., Huang, Q., Zhang, Y.C.: Synthesis of Sn-doped ZnO nanorods and their photocatalytic properties. Mater. Res. Bull. 46, 1107–1112 (2011)
45. Karunakaran, C., Gomathisankar, P., Manikandan, G.: Preparation and characterization of antimicrobial Ce-doped ZnO nanoparticles for photocatalytic detoxification of cyanide. Mater. Chem. Phys. 123, 585–594 (2010)
46. Barick, K. C., Singh, S., Aslamb, M., Bahadur, D.: Porosity and photocatalytic studies of transition metal doped ZnO nanoclusters. Microporous. Mesoporous. Mater. 134, 195–202 (2010)
47. 2 synthesized by a hydrothermal method. Mater. Chem. Phys. 112, 47–51 (2008) DOI: 10.1016/j.matchemphys.2008.05.005
48. Fallah Moafi, H., Zanjanchi, M.A., Fallah Shojaie, A.: Tungsten-doped ZnO nanocomposite: Synthesis, characterization, and highly active photocatalyst toward dye photodegradation. Mater. Chem. Phys. 139, 856–864 (2013) DOI: 10.1016/j.matchemphys.2013.02.044
49. +-montmorillonite (SANM): A novel, efficient and recyclable catalyst for the chemoselective N-Boc protection of amines in solvent less media. Catal. Commun. 12, 1088–1094 (2011) DOI: 10.1016/j.catcom.2011.03.030
50. 4 as a new, efficient and recyclable catalyst for the chemoselectivetrimethylsilylation of alcohols, phenols and deprotection of silyl ethers. Catal. Commun. 18, 5–10 (2012) DOI: 10.1016/j.catcom.2011.11.002
51. 3 nano-particles: Introduction of a mild, efficient and reusable catalyst for some of the multi-component reactions. C. R. Chimie. 16, 945–955 (2013) DOI: 10.1016/j.crci.2013.02.019
52. Tavakoli-Hoseini, N., Heravi, M.M., Bamoharram, F.F., Davoodnia, A., Ghassemzadeh, M.: An unexpected tetracyclic product isolated during the synthesis of biscoumarins catalyzed by [MIM(CH2)4SO3H][HSO4]: Characterization and X-ray crystal structure of 7-(2-hydroxy-4-oxo-4H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one. J. Mol. Liq. 163, 122–127 (2011) DOI: 10.1016/j.molliq.2011.08.007
53. Khurana, J.M., Vij, K.: Nickel nanoparticles: A highly efficient catalyst for one pot synthesis of tetraketones and biscoumarins. J. Chem. Sci. 124, 907–912 (2012) DOI: 10.1007/s12039-012-0275-8
54. Al-Kadasi, A.M.A., Nazeruddin, G.M.: Ultrasound assisted catalyst-free one-pot synthesis of biscoumarins in neat water. Int. J. Chem. Sci. 10, 324–330 (2012)
55. Niknam, K., Jamali, A.: Silica-bonded N-propylpiperazine sodium n-propionate as recyclable basic catalyst for synthesis of 3,4-dihydropyrano[c]chromene derivatives and biscoumarins. Chin. J. Catal. 33, 319–326 (2012)
56. Manolov, I., Maichle-Moessmer, C., Nicolova, I., Danchev, N.: Synthesis and anticoagulant activities of substituted 2,4-diketochromans, biscoumarins, and chromanocoumarins. Arch. Pharm. Chem. Life. Sci. 339, 319–326 (2006) DOI: 10.1002/ardp.200500149
57. Manolov, I., Maichle-Moessmer, C., Danchev, N.: Toxicological and pharmacological investigations of 4-hydroxycoumarin derivatives. Eur. J. Med. Chem. 41, 882–890 (2006) DOI: 10.1016/j.ejmech.2006.03.007
58. 3H) as a highly efficient and reusable catalyst for the synthesis of some of bisheterocyclic compounds. RSC Adv. 3, 24046–24053 (2013) DOI: 10.1039/c3ra44053b
59. Kidwai, M., Bansal, V., Mothsra, P., Saxena, S., Somvanshi, R.K., Dey, S., Singh, T.P.: Molecular iodine: a versatile catalyst for the synthesis of bis(4-hydroxycoumarin) methanes in water. J. Mol. Catal. A. 265, 76–81 (2007) DOI: 10.1016/j.molcata.2006.11.054
60. Tabatabaeian, K., Heidari, H., Khorshidi, A.R., Mamaghani, M., Mahmoodi, N.O.: Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium(III) chloride hydrate as a versatile homogeneous catalyst. J. Serb. Chem. Soc. 77, 407–413 (2012) DOI: 10.2298/JSC110427189T