A novel nanocomposite, H₄SiW₁₂O₄₀ immobilised magnetic chitosan (HSiW-MC) was prepared via a facile procedure in one-pot fashion. This composite was fully characterised using several methods including, Fourier transform infrared spectroscopy, X-ray diffraction, energy-dispersive X-ray spectroscopy and scanning electron microscopy. It was applied as a novel catalyst in two three components reaction involving, dimedone, differently substituted aryl aldehydes and either 3-amino-1,2,4-triazole or 2-amino benzimidazole to afford the corresponding [1,2,4]triazolo/benzimidazolo quinazolinone derivatives. It showed excellent performance in the aforementioned reaction with the high yield of 96%. Also, the effect of HSiW-MC amount, catalysts, solvents and temperatures were studied and the best results were obtained in CH₃CN in the presence of HSiW-MC (0.04 g) under refluxing conditions.

References

1. 1)
  - 24. Bamoharram, F.F., Niknezhad, S.H., Baharara, J., et al: ‘Amine-functionalized nanosilica-supported Dawson heteropolyacid: an eco-friendly and reusable photocatalyst for photodegradation of malachite green’, J. Nanostruct. Chem., 2014, 4, p. 88 (doi: 10.1007/s40097-014-0088-z).
2. 2)
  - 18. Heravi, M.M., Fard, M.V., Faghihi, Z.: ‘Heteropoly acids-catalyzed organic reactions in water: doubly green reactions’, Green Chem. Lett. Rev., 2013, 6, (4), pp. 282–300 (doi: 10.1080/17518253.2013.846415).
3. 3)
  - 32. Santamaria, M., Pecoraro, C.M., Quarto, F.D., et al: ‘Chitosanephosphotungstic acid complex as membranes for low temperature H2-O2 fuel cell’, J. Power Source, 2015, 276, pp. 189–194 (doi: 10.1016/j.jpowsour.2014.11.147).
4. 4)
  - 39. Maleki, A., Kamalzare, M., Aghaei, M.: ‘Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst’, J. Nanostruct. Chem., 2015, 5, pp. 95–105 (doi: 10.1007/s40097-014-0140-z).
5. 5)
  - 20. Sadjadi, S., Heravi, M.M.: ‘Recent advances in applications of POMs and their hybrids in catalysis’, Curr. Org. Chem., 2016, 20, (13), pp. 1404–1444 (doi: 10.2174/1385272820666160216225330).
6. 6)
  - 53. Lei, Z., Pang, X., Li, N., et al: ‘A novel two-step modifying process for preparation of chitosan-coated Fe3O4/SiO2 microspheres’, J. Mater. Proc. Technol., 2009, 209, pp. 3218–3225 (doi: 10.1016/j.jmatprotec.2008.07.044).
7. 7)
  - 58. Heravi, M.M., Tajbakhsh, M., Ahmadi, A.N., et al: ‘Zeolites. Efficient and eco-friendly catalysts for the synthesis of benzimidazoles’, Monatsh. Chem., 2005, 137, (2), pp. 175–179 (doi: 10.1007/s00706-005-0407-7).
8. 8)
  - 45. Heravi, M.M., Derikvand, F., Ranjbar, L.: ‘Sulfamic acid-catalyzed, three-component, one-pot synthesis of [1,2,4]triazolo/benzimidazolo quinazolinone derivatives’, Synth. Commun., 2010, 40, (5), pp. 677–685 (doi: 10.1080/00397910903009489).
9. 9)
  - 38. Maleki, A., Kamalzare, M.: ‘An efficient synthesis of benzodiazepine derivatives via a one-pot, three-component reaction accelerated by a chitosan-supported superparamagnetic iron oxide nanocomposite’, Tetrahedron Lett., 2014, 55, (50), pp. 6931–6934 (doi: 10.1016/j.tetlet.2014.10.120).
10. 10)
  - 33. Maleki, A., Aghaei, M.: ‘Ultrasonic assisted synergetic green synthesis of polycyclic Imidazo(thiazolo)pyrimidines by using Fe3O4@clay core–shell’, Ultrason. Sonochem., 2016, In Press.
11. 11)
  - 16. Heravi, M.M., Hashemi, E., Beheshtiha, Y.S., et al: ‘Solvent-free multicomponent reactions using the novel N-sulfonic acid modified poly(styrene-maleic anhydride) as a solid acid catalyst’, J. Mol. Catal. A, Chem., 2014, 392, pp. 173–180 (doi: 10.1016/j.molcata.2014.04.024).
12. 12)
  - 11. Heravi, M.M., Khaghaninejad, S., Nazari, N.: ‘Chapter five – Bischler-Napieralski reaction in the syntheses of isoquinolines’, Adv. Heterocycl. Chem., 2014, 112, pp. 183–234 (doi: 10.1016/B978-0-12-800171-4.00005-6).
13. 13)
  - 52. Talebian-Kiakalaieh, A., Amin, N.A.S., Zakaria, Z.Y.: ‘Gas phase selective conversion of glycerol to acrolein over supported silicotungstic acid catalyst’, J. Ind. Eng. Chem., 2016, 34, pp. 300–312 (doi: 10.1016/j.jiec.2015.11.024).
14. 14)
  - 34. Maleki, A., Movahed, H., Ravaghi, P.: ‘Magnetic cellulose/Ag as a novel eco-friendly nanobiocomposite to catalyze synthesis of chromene-linked nicotinonitriles’, Carbohyd. Polym., 2017, 156, pp. 259–267 (doi: 10.1016/j.carbpol.2016.09.002).
15. 15)
  - 2. Garay, A.L., Pichon, A., James, S.L.: ‘Solvent-free synthesis of metal complexes’, Chem. Soc. Rev., 2007, 36, pp. 846–855 (doi: 10.1039/b600363j).
16. 16)
  - 6. Ram, V.J., Srimal, R.C., Kushwaha, D.S., et al: ‘Chemotherapeutic agents. XIX. Synthesis of [1,2,4]-triazoloquinazolinones and related compounds as antihypertensive agents’, J. Prakt. Chem., 1990, 332, pp. 629–639 (doi: 10.1002/prac.19903320507).
17. 17)
  - 4. Rakesh, K.P., Manukumar, H.M., Gowda, D.C.: ‘Schiff's bases of quinazolinone derivatives: Synthesis and SAR studies of a novel series of potential anti-inflammatory and antioxidants’, Bioorg. Med. Chem. Lett., 2015, 25, (5), pp. 1072–1077 (doi: 10.1016/j.bmcl.2015.01.010).
18. 18)
  - 35. Maleki, A., Aghaei, M., Hafizi-Atabak, H.R., et al: ‘Ultrasonic treatment of CoFe2O4@B2O3-SiO2 as a new hybrid magnetic composite nanostructure and catalytic application in the synthesis of dihydroquinazolinones’, Ultrason. Sonochem., 2017, 37, pp. 260–266 (doi: 10.1016/j.ultsonch.2017.01.022).
19. 19)
  - 1. Li, R.-K., Yang, Q.-L., Liu, Y., et al: ‘A novel and green synthesis of indolone-N-amino acid derivatives via the Passerini three-component reactions in water’, Chin. Chem. Lett., 2016, 27, (3), pp. 345–348 (doi: 10.1016/j.cclet.2015.11.008).
20. 20)
  - 41. Tanhaei, B., Ayati, A., Bamoharram, F.F., et al: ‘A novel magnetic Preyssler acid grafted chitosan nano adsorbent: synthesis, characterization and adsorption activity’, J. Chem. Technol. Biotechnol., 2016, 91, (5), pp. 1452–1460 (doi: 10.1002/jctb.4742).
21. 21)
  - 28. Wang, Q., Jiao, D., Bai, Y., et al: ‘Immobilized heteropolyacids with zeolite (MCM-41) to enhance photocatalytic performance of BiOBr’, Mater. Lett., 2015, 161, pp. 267–270 (doi: 10.1016/j.matlet.2015.08.111).
22. 22)
  - 26. Ayati, A., Tanhaei, B., Bamoharram, F.F., et al: ‘Photocatalytic degradation of nitrobenzene by gold nanoparticles decorated polyoxometalate immobilized TiO2 nanotubes’, Sep. Purif. Technol., 2016, 171, pp. 62–68 (doi: 10.1016/j.seppur.2016.07.015).
23. 23)
  - 7. Heravi, M.M., Talaei, B.: ‘Chapter four – ketenes as privileged synthons in the syntheses of heterocyclic compounds. Part 1: three- and four-membered heterocycles’, Adv. Heterocycl. Chem., 2014, 113, pp. 143–244 (doi: 10.1016/B978-0-12-800170-7.00004-3).
24. 24)
  - 55. Heravi, M.M., Bakhtiari, K., Daroogheha, Z., et al: ‘An efficient synthesis of 2,4,6-triarylpyridines catalyzed by heteropolyacid under solvent-free conditions’, Catal. Commun., 2007, 8, (12), pp. 1991–1994 (doi: 10.1016/j.catcom.2007.03.028).
25. 25)
  - 22. Li, T., Zhang, Z., Li, W., et al: ‘H4SiW12O40/polymethylmethacrylate/polyvinyl alcohol sandwich nanofibrous membrane with enhanced photocatalytic activity’, Colloids Surf. A, Physicochem. Eng. Aspects, 2016, 489, pp. 289–296 (doi: 10.1016/j.colsurfa.2015.10.061).
26. 26)
  - 23. Kozhevnikov, I.V.: ‘Catalysis by heteropoly acids and multicomponent polyoxometalates in liquid-phase reactions’, Chem. Rev., 1998, 98, pp. 171–198 (doi: 10.1021/cr960400y).
27. 27)
  - 14. Mirsafaei, R., Heravi, M.M., Ahmadi, S., et al: ‘In situ prepared copper nanoparticles on modified KIT-5 as an efficient recyclable catalyst and its applications in click reactions in water’, J. Mol. Catal. A, Chem., 2015, 402, pp. 100–108 (doi: 10.1016/j.molcata.2015.03.006).
28. 28)
  - 40. Maleki, A.: ‘Efficient synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in the presence of ferrite/chitosan as a green and reusable nanocatalyst’, Int. J. Nanosci. Nanotechnol., 2016, 12, pp. 215–222.
29. 29)
  - 5. He, D., Wang, M., Zhao, S., et al: ‘Pharmaceutical prospects of naturally occurring quinazolinone and its derivatives’, Fitoterapia, 2017, 119, pp. 136–149 (doi: 10.1016/j.fitote.2017.05.001).
30. 30)
  - 48. Mousavi, M.R., Maghsoodlou, M.T., Hazeri, N., et al: ‘A simple, economical, and environmentally benign protocol for the synthesis of [1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one and hexahydro[4,5]benzimidazolo[2,1-b]quinazolinone derivatives’, J. Iran. Chem. Soc., 2015, 12, (8), pp. 1419–1424 (doi: 10.1007/s13738-015-0609-9).
31. 31)
  - 44. Ayati, A., Heravi, M.M., Daraie, M., et al: ‘H3PMo12O40 immobilized chitosan/Fe3O4 as a novel efficient, green and recyclable nanocatalyst in the synthesis of pyrano-pyrazole derivatives’, J. Iran Chem. Soc., 2016, accepted.
32. 32)
  - 60. Heravi, M.M., Alishiri, T.: ‘Chapter one – dimethyl acetylenedicarboxylate as a building block in heterocyclic synthesis’, Adv. Heterocycl. Chem., 2014, 113, pp. 1–66 (doi: 10.1016/B978-0-12-800170-7.00001-8).
33. 33)
  - 49. Beerappa, M., Shivashankar, K.: ‘Multicomponent reaction of benzyl halides: synthesis of [1,2,4]triazolo/benzimidazolo quinazolinones’, Synth. Commun., 2016, 46, pp. 421–432 (doi: 10.1080/00397911.2016.1140784).
34. 34)
  - 27. Kang, T.H., Choi, J.H., Bang, Y., et al: ‘Dehydration of glycerin to acrolein over H3PW12O40 heteropolyacid catalyst supported on silica-alumina’, J. Mol. Catal. A, Chem., 2015, 369, pp. 282–289 (doi: 10.1016/j.molcata.2014.10.015).
35. 35)
  - 50. Jin, H., Yi, X., Sun, X., et al: ‘Influence of H4SiW12O40 loading on hydrocracking activity of non-sulfide Ni-H4SiW12O40/SiO2 catalysts’, Fuel, 2010, 89, pp. 1953–1960 (doi: 10.1016/j.fuel.2009.11.031).
36. 36)
  - 29. Pecoraro, C.M., Santamaria, M., Bocchetta, P., et al: ‘Influence of synthesis conditions on the performance of chitosan-heteropolyacid complexes as membranes for low temperature H2-O2 fuel cell’, Int. J. Hydrogen Energy, 2015, 40, (42), pp. 14616–14626 (doi: 10.1016/j.ijhydene.2015.06.083).
37. 37)
  - 9. Heravi, M.M., Vavsari, V.F.: ‘Chapter two – recent advances in application of amino acids: key building blocks in design and syntheses of heterocyclic compounds’, Adv. Heterocycl. Chem., 2015, 114, pp. 77–145 (doi: 10.1016/bs.aihch.2015.02.002).
38. 38)
  - 8. Heravi, M.M., Talaei, B.: ‘Chapter three – ketenes as privileged synthons in the syntheses of heterocyclic compounds part 2: five-membered heterocycles’, Adv. Heterocycl. Chem., 2015, 114, pp. 147–225 (doi: 10.1016/bs.aihch.2015.02.001).
39. 39)
  - 46. Mousavi, M.R., Maghsoodlou, M.T.: ‘Catalytic systems containing p-toluenesulfonic acid monohydrate catalyzed the synthesis of triazoloquinazolinone and benzimidazoquinazolinone derivatives’, Monatsh. Chem., 2014, 145, pp. 1967–1973 (doi: 10.1007/s00706-014-1273-y).
40. 40)
  - 59. Heravi, M.M., Daraie, M., Behbahani, F.K., et al: ‘Green and novel protocol for one-pot synthesis of β-acetamido carbonyl compounds using Mn(bpdo)2Cl2/MCM-41 catalyst’, Synth. Commun., 2010, 40, (8), pp. 1180–1186 (doi: 10.1080/00397910903051267).
41. 41)
  - 19. Heravi, M.M., Sadjadi, S.: ‘Recent developments in use of heteropolyacids, their salts and polyoxometalates in organic synthesis’, J. Iran. Chem. Soc., 2009, 6, (1), pp. 1–54 (doi: 10.1007/BF03246501).
42. 42)
  - 3. Ismail, , Kuthati, B., Thalari, G., et al: ‘Synthesis of novel spiro[pyrazolo[4,3-d]pyrimidinones and spiro[benzo[4,5]thieno[2,3-d]pyrimidine-2,3′-indoline]-2′,4(3H)-diones and their evaluation for anticancer activity’, Bioorg. Med. Chem. Lett., 2017, 27, (6), pp. 1446–1450 (doi: 10.1016/j.bmcl.2017.01.088).
43. 43)
  - 17. Heravi, M.M., Khorasani, M., Derikvand, F., et al: ‘Highly efficient synthesis of coumarin derivatives in the presence of H14[NaP5W30O110] as a green and reusable catalyst’, Catal. Commun., 2007, 8, (12), pp. 1886–1890 (doi: 10.1016/j.catcom.2007.02.030).
44. 44)
  - 13. Heravi, M.M., Khaghaninejad, S., Mostofi, M.: ‘Chapter one – Pechmann reaction in the synthesis of coumarin derivatives’, Adv. Heterocycl. Chem., 2014, 112, pp. 1–50 (doi: 10.1016/B978-0-12-800171-4.00001-9).
45. 45)
  - 36. Maleki, A., Aghaei, M., Ghamari, N.: ‘Facile synthesis of tetrahydrobenzoxanthenones via a one-pot three-component reaction using an eco-friendly and magnetized biopolymer chitosan-based heterogeneous nanocatalyst’, Appl. Organometal. Chem., 2016, 30, pp. 939–942 (doi: 10.1002/aoc.3524).
46. 46)
  - 12. Khaghaninejad, S., Heravi, M.M.: ‘Chapter three – Paal-Knorr reaction in the synthesis of heterocyclic compounds’, Adv. Heterocycl. Chem., 2014, 111, pp. 95–146 (doi: 10.1016/B978-0-12-420160-6.00003-3).
47. 47)
  - 56. Heravi, M.M., Sadjadi, S., Oskooie, H.A., et al: ‘The synthesis of coumarin-3-carboxylic acids and 3-acetyl-coumarin derivatives using heteropolyacids as heterogeneous and recyclable catalysts’, Catal. Commun., 2008, 9, (3), pp. 470–474 (doi: 10.1016/j.catcom.2007.07.005).
48. 48)
  - 10. Heravi, M.M., Zadsirjan, V.: ‘Chapter five – recent advances in the synthesis of Benzo[b]furans’, Adv. Heterocycl. Chem., 2015, 117, pp. 261–376 (doi: 10.1016/bs.aihch.2015.08.003).
49. 49)
  - 47. Amoozadeh, A., Rahmani, S.: ‘Nano-WO3-supported sulfonic acid: new, efficient and high reusable heterogeneous nano catalyst’, J. Mol. Catal. A, Chem., 2015, 396, pp. 96–107 (doi: 10.1016/j.molcata.2014.09.020).
50. 50)
  - 25. Ayati, A., Ahmadpour, A., Bamoharram, F.F., et al: ‘Novel Au NPs/Preyssler acid/TiO2 nanocomposite for the photocatalytic removal of azo dye’, Sep. Purif. Technol., 2014, 133, pp. 415–420 (doi: 10.1016/j.seppur.2014.06.055).
51. 51)
  - 43. Kong, A., Wang, P., Zhang, H., et al: ‘One-pot fabrication of magnetically recoverable acid nanocatalyst, heteropolyacids/chitosan/Fe3O4, and its catalytic performance’, Appl. Phys. A, Gen., 2012, 417–418, pp. 183–189.
52. 52)
  - 37. Maleki, A., Aghaei, M., Ghamari, N.: ‘Synthesis of benzimidazolo[2,3-b]quinazolinone derivatives via a one-pot multicomponent reaction promoted by a chitosan-based composite magnetic nanocatalyst’, Chem. Lett., 2015, 3, pp. 259–261 (doi: 10.1246/cl.141074).
53. 53)
  - 54. Safari, J., Javadian, L.: ‘Chitosan decorated Fe3O4 nanoparticles as a magnetic catalyst in the synthesis of phenytoin derivatives’, RSC Adv., 2014, 4, pp. 48973–48979 (doi: 10.1039/C4RA06618A).
54. 54)
  - 30. Sashiwa, H., Aiba, S.: ‘Chemically modified chitin and chitosan as biomaterials’, Prog. Polym. Sci., 2004, 29, pp. 887–908 (doi: 10.1016/j.progpolymsci.2004.04.001).
55. 55)
  - 21. Bamoharram, F.F., Ahmadpour, A., Heravi, M.M., et al: ‘Recent advances in application of polyoxometalates for the synthesis of nanoparticles’, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 2012, 42, (2), pp. 209–230 (doi: 10.1080/15533174.2011.609849).
56. 56)
  - 51. Pisanic, T.R., Blackwell, J.D., Shubayev, V.I., et al: ‘Nanotoxicity of iron oxide nanoparticle internalization in growing neurons’, Biomaterials, 2007, 28, pp. 2572–2581 (doi: 10.1016/j.biomaterials.2007.01.043).
57. 57)
  - 31. Tanhaei, B., Ayati, A., Lahtinen, M., et al: ‘Preparation and characterization of a novel chitosan/Al2O3/magnetite nanoparticles composite adsorbent for kinetic, thermodynamic and isotherm studies of methyl orange adsorption’, Chem. Eng. J., 2015, 259, pp. 1–10 (doi: 10.1016/j.cej.2014.07.109).
58. 58)
  - 57. Heravi, M.M., Behbahani, F.K., Daraie, M., et al: ‘Fe(ClO4)3·6H2O: a mild and efficient catalyst for one-pot three component synthesis of β-acetamido carbonyl compounds under solvent-free conditions’, Mol. Divers., 2009, 13, (3), pp. 375–378 (doi: 10.1007/s11030-009-9118-z).
59. 59)
  - 42. Tanhaei, B., Ayati, A., Bamoharram, F.F., et al: ‘Magnetic EDTA-Preyssler cross linked chitosan core–shell composite for the removal of Pb(II) ions removal’, Clean Air Soil Water, 2016, accepted.
60. 60)
  - 15. Heravi, M.M., Hashemi, E., Beheshtiha, Y.S., et al: ‘PdCl2 on modified poly(styrene-co-maleic anhydride): a highly active and recyclable catalyst for the Suzuki-Miyaura and Sonogashira reactions’, J. Mol. Catal. A, Chem., 2014, 394, pp. 74–82 (doi: 10.1016/j.molcata.2014.07.001).

H₄[W₁₂SiO₄₀] grafted on magnetic chitosan: a green nanocatalyst for the synthesis of [1,2,4]triazolo/benzimidazolo quinazolinone derivatives

References

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H₄[W₁₂SiO₄₀] grafted on magnetic chitosan: a green nanocatalyst for the synthesis of [1,2,4]triazolo/benzimidazolo quinazolinone derivatives