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The raise of SBA-SO3H catalytic activity by inducing ultrasound irradiation in the multicomponent syntheses

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Abstract

This work shows that ultrasound irradiations and mesoporous SBA-SO3H together can have a synergic effect on the catalysis of highly substituted imidazole, dihydropyrimidinone and dihydropyridine derivatives syntheses via multicomponent coupling method. In this paper, we have presented a system which is combination of mesoporous nanoreactors and ultrasonic irradiation for efficient synthesis of the biologically interesting heterocycles. Induction of ultrasonication on SBA-SO3H has led to a remarkable acceleration on the mass transfer through the mesochannels (or nanoreactors). This modification on the mesochannels caused to development of mild conditions, high selectivity and tolerance with various functional groups and high yields in short reaction time.

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References

  1. H. Mootabadi, B. Salamatinia, S. Bhatia, A.Z. Abdullah, Ultrasonic-assisted biodiesel production process from palm oil using alkaline earth metal oxides as the heterogeneous catalysts. Fuel 89, 1818–1825 (2010)

    Article  CAS  Google Scholar 

  2. Y.C. Fiamegos, C.G. Nanos, C.D. Stalikas, Ultrasonic-assisted derivatization reaction of amino acids prior to their determination in urine by using single-drop microextraction in conjunction with gas chromatography. J. Chromatogr. B 813, 89–94 (2004)

    Article  CAS  Google Scholar 

  3. D. Kumar, G. Kumar, C. Singh, Ultrasonic-assisted transesterification of Jatropha curcus oil using solid catalyst, Na/SiO2. Ultrason. Sonochem. 17, 839–844 (2010)

    Article  CAS  Google Scholar 

  4. R.S. Varma, H.M. Meshram, Solid state cleavage of semicarbazones and phenylhydrazones with ammonium persulfate-clay using microwave or ultrasonic irradiation. Tetrahedron Lett. 38, 7973–7976 (1997)

    Article  CAS  Google Scholar 

  5. L.-P. Jiang, S. Xu, J.-M. Zhu, J.-R. Zhang, J.-J. Zhu, H.-Y. Chen, Ultrasonic-assisted synthesis of monodisperse single-crystalline silver nanoplates and gold nanorings. Inorg. Chem. 43, 5877–5883 (2004)

    Article  CAS  Google Scholar 

  6. B. Salamatinia, H. Mootabadi, S. Bhatia, A.Z. Abdullah, Optimization of ultrasonic-assisted heterogeneous biodiesel production from palm oil: a response surface methodology approach. Fuel Process. Technol. 91, 441–448 (2010)

    Article  CAS  Google Scholar 

  7. A. Taguchi, F. Schüth, Ordered mesoporous materials in catalysis. Microporous Mesoporous Mater. 77, 1–45 (2005)

    Article  CAS  Google Scholar 

  8. S. Rostamnia, E. Doustkhah, Nanoporous silica-supported organocatalyst: a heterogeneous and green hybrid catalyst for organic transformations. RSC Adv. 4, 28238–28248 (2014)

    Article  CAS  Google Scholar 

  9. M. Nandi, J. Mondal, K. Sarkar, Y. Yamauchi, A. Bhaumik, Highly ordered acid functionalized SBA-15: a novel organocatalyst for the preparation of xanthenes. Chem. Commun. 47, 6677–6679 (2011)

    Article  CAS  Google Scholar 

  10. J.A. Melero, R. van Grieken, G. Morales, Advances in the synthesis and catalytic applications of organosulfonic-functionalized mesostructured materials. Chem. Rev. 106, 3790–3812 (2006)

    Article  CAS  Google Scholar 

  11. S. Rostamnia, F. Pourhassan, The SBA-15/SO3H nanoreactor as a highly efficient and reusable catalyst for diketene-based, four-component synthesis of polyhydroquinolines and dihydropyridines under neat conditions. Chin. Chem. Lett. 24, 401–403 (2013)

    Article  CAS  Google Scholar 

  12. J.A. Melero, L.F. Bautista, J. Iglesias, G. Morales, R. Sánchez-Vázquez, K. Wilson, A.F. Lee, New insights in the deactivation of sulfonic modified SBA-15 catalysts for biodiesel production from low-grade oleaginous feedstock. Appl. Catal. A Gen. 488, 111–118 (2014)

    Article  CAS  Google Scholar 

  13. C. Pirez, A. Lee, J. Manayil, C. Parlett, K. Wilson, Hydrothermal saline promoted grafting: a route to sulfonic acid SBA-15 silica with ultra-high acid site loading for biodiesel synthesis. Green Chem. 16, 4506–4509 (2014)

    Article  CAS  Google Scholar 

  14. S. Rostamnia, E. Doustkhah, A. Nuri, Hexafluoroisopropanol dispersed into the nanoporous SBA-15 (HFIP/SBA-15) as a rapid, metal-free, highly reusable and suitable combined catalyst for domino cyclization process in chemoselective preparation of alkyl rhodanines. J. Fluor. Chem. 153, 1–6 (2013)

    Article  CAS  Google Scholar 

  15. S. Rostamnia, E. Doustkhah, A mesoporous silica/fluorinated alcohol adduct: an efficient metal-free, three-component synthesis of indazolophthalazinetrione heterocycles using a reusable nanoporous/trifluoroethanol adduct (SBA-15/TFE). Tetrahedron Lett. 55, 2508–2512 (2014)

    Article  CAS  Google Scholar 

  16. S. Rostamnia, E. Doustkhaha, Increased SBA-15–SO3H catalytic activity through hydrophilic/hydrophobic fluoroalkyl-chained alcohols (RFOH/SBA-15–Pr-SO3H). Synlett 26, 1345-1347 (2015)

    Article  Google Scholar 

  17. S. Rostamnia, H. Xin, X. Liu, K. Lamei, Simultaneously application of SBA-15 sulfonic acid nanoreactor and ultrasonic irradiation as a very useful novel combined catalytic system: an ultra-fast, selective, reusable and waste-free green approach. J. Mol. Catal. A: Chem. 374, 85–93 (2013)

    Article  Google Scholar 

  18. D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores. Science 279, 548–552 (1998)

    Article  CAS  Google Scholar 

  19. A. Da Settimo, G. Primofiore, F. Da Settimo, L. Calzolari, P. Cazzulani, A. Passoni, O. Tofanetti, 1-Substituted 2-benzylaminobenzimidazole derivatives: compounds with H 1-antihistaminic activity. Eur. J. Med. Chem. 27, 395–400 (1992)

    Article  Google Scholar 

  20. N. Koukabi, E. Kolvari, A. Khazaei, M.A. Zolfigol, B. Shirmardi-Shaghasemi, H.R. Khavasi, Hantzsch reaction on free nano-Fe2O3 catalyst: excellent reactivity combined with facile catalyst recovery and recyclability. Chem. Commun. 47, 9230–9232 (2011)

    Article  CAS  Google Scholar 

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Correspondence to Esmail Doustkhah, Sadegh Rostamnia or Asadollah Hassankhani.

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Doustkhah, E., Rostamnia, S. & Hassankhani, A. The raise of SBA-SO3H catalytic activity by inducing ultrasound irradiation in the multicomponent syntheses. J Porous Mater 23, 549–556 (2016). https://doi.org/10.1007/s10934-015-0108-5

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