Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2018, Article ID 2785067, 6 pages
https://doi.org/10.1155/2018/2785067
Research Article

MCM-41-Accelerated PWA Catalysis of Friedel-Crafts Reaction of Indoles and Isatins

1Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education & Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China
2Department of Chemistry and Centre for Pharmacy, University of Bergen, 5020 Bergen, Norway

Correspondence should be addressed to YongHai Hui; moc.621@79iahyh and Wei Wang; on.biu@gnaw.iew

Received 22 July 2017; Accepted 1 November 2017; Published 18 January 2018

Academic Editor: Pasquale Longo

Copyright © 2018 Liuzhuang Xing et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. G. Sartori and R. Maggi, “Use of solid catalysts in Friedel-Crafts acylation reactions,” Chemical Reviews, vol. 111, no. 20, pp. 181–214, 2011. View at Google Scholar
  2. X. Liang, S. Z. Jiang, K. Wei, and Y. R. Yang, “Enantioselective total synthesis of (-)-Alstoscholarisine A,” Journal of the American Chemical Society, vol. 138, no. 8, pp. 2560–2562, 2016. View at Publisher · View at Google Scholar · View at Scopus
  3. G. R. Pettit, J. D. Searcy, R. Tan et al., “Antineoplastic Agents. 585. Isolation of Bridelia ferruginea Anticancer Podophyllotoxins and Synthesis of 4-Aza-podophyllotoxin Structural Modifications,” Journal of Natural Products, vol. 79, no. 3, pp. 507–518, 2016. View at Publisher · View at Google Scholar · View at Scopus
  4. H. Gurer-Orhan, C. Karaaslan, S. Ozcan et al., “Novel indole-based melatonin analogues: evaluation of antioxidant activity and protective effect against amyloid β-induced damage,” Bioorganic & Medicinal Chemistry, vol. 24, no. 8, pp. 1658–1664, 2016. View at Publisher · View at Google Scholar · View at Scopus
  5. M. S. Shmidt, I. A. Perillo, A. Camelli, M. A. Fernández, and M. M. Blanco, “Polyfunctional 4-quinolinones. Synthesis of 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines,” Tetrahedron Letters, vol. 57, no. 9, pp. 1022–1026, 2016. View at Publisher · View at Google Scholar · View at Scopus
  6. D. Sriram, P. Yogeeswari, N. S. Myneedu, and V. Saraswat, “Abacavir prodrugs: microwave-assisted synthesis and their evaluation of anti-HIV activities,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 8, pp. 2127–2129, 2006. View at Publisher · View at Google Scholar · View at Scopus
  7. T. Jiang, K. L. Kuhen, K. Wolff et al., “Design, synthesis and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part I,” Bioorganic & Medicinal Chemistry Letters, vol. 16, no. 8, pp. 2105–2108, 2006. View at Publisher · View at Google Scholar · View at Scopus
  8. A. Kamal, Y. V. V. Srikanth, M. N. A. Khan, T. B. Shaik, and M. Ashraf, “Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity,” Bioorganic & Medicinal Chemistry Letters, vol. 20, no. 17, pp. 5229–5231, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. J. Azizian, A. A. Mohammadi, N. Karimi, M. R. Mohammadizadeh, and A. R. Karimi, “Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives,” Catalysis Communications, vol. 7, no. 10, pp. 752–755, 2006. View at Publisher · View at Google Scholar · View at Scopus
  10. G. Brahmachari and B. Banerjee, “Facile and one-pot access of 3,3-bis(indol-3-yl)indolin-2-ones and 2,2-bis(indol-3-yl)acenaphthylen-1(2H)-one derivatives via an eco- friendly pseudo-multicomponent reaction at room temperature using sulfamic acid as an organo-catalyst,” ACS Sustainable Chemistry & Engineering, vol. 2, no. 12, pp. 2802–2812, 2014. View at Publisher · View at Google Scholar · View at Scopus
  11. P. Paira, A. Hazra, S. Kumar et al., “Efficient synthesis of 3,3-diheteroaromatic oxindole analogues and their in vitro evaluation for spermicidal potential,” Bioorganic & Medicinal Chemistry Letters, vol. 19, no. 16, pp. 4786–4789, 2009. View at Publisher · View at Google Scholar · View at Scopus
  12. C. Praveen, A. Ayyanar, and P. T. Perumal, “Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma,” Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 14, pp. 4170–4173, 2011. View at Publisher · View at Google Scholar · View at Scopus
  13. K. Rad-Moghadam, M. Sharifi-Kiasaraie, and H. Taheri-Amlashi, “Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids,” Tetrahedron, vol. 66, no. 13, pp. 2316–2321, 2010. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Y. Wang and S. J. Ji, “Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation,” Tetrahedron, vol. 62, no. 7, pp. 1527–1535, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. Y. A. Tayade, D. R. Patil, Y. B. Wagh, A. D. Jangle, and D. S. Dalal, “An efficient synthesis of 3-indolyl-3-hydroxy oxindoles and 3,3-di(indolyl)indolin-2-ones catalyzed by sulfonated β-CD as a supramolecular catalyst in water,” Tetrahedron Letters, vol. 56, no. 5, pp. 666–673, 2015. View at Publisher · View at Google Scholar · View at Scopus
  16. Y. Sarrafi, K. Alimohammadi, M. Sadatshahabi, and N. Norozipoor, “An improved catalytic method for the synthesis of 3,3-di(indolyl)oxindoles using Amberlyst 15 as a heterogeneous and reusable catalyst in water,” Monatshefte für Chemie, vol. 143, no. 11, pp. 1519–1522, 2012. View at Publisher · View at Google Scholar · View at Scopus
  17. S. Z. Sayyed-Alangi and Z. Hossaini, “ZnO nanorods as an efficient catalyst for the green synthesis of indole derivatives using isatoic anhydride,” Chemistry of Heterocyclic Compounds, vol. 51, no. 6, pp. 541–544, 2015. View at Publisher · View at Google Scholar · View at Scopus
  18. K. Sugino, N. Oya, N. Yoshie, and M. Ogura, “A simple modification creates a great difference: new solid-base catalyst using methylated N-substituted SBA-15,” Journal of the American Chemical Society, vol. 133, no. 50, pp. 20030–20032, 2011. View at Publisher · View at Google Scholar · View at Scopus
  19. Suryani, C. M. Chang, Y. L. Liu, and Y. M. Lee, “Polybenzimidazole membranes modified with polyelectrolyte-functionalized multiwalled carbon nanotubes for proton exchange membrane fuel cells,” Journal of Materials Chemistry, vol. 21, no. 20, pp. 7480–7486, 2011. View at Publisher · View at Google Scholar · View at Scopus
  20. X. Li, G. Qin, Y. Wang, and W. Wei, “Keggin-type phosphotungstic acid supported on mesoporous SiO2–Al2O3 aerogel like beads and their application in the isopropylation of naphthalene,” Journal of Sol-Gel Science and Technology, vol. 72, no. 2, pp. 405–414, 2014. View at Publisher · View at Google Scholar · View at Scopus
  21. K. Fan, Y. H. Hui, X. H. Hu, W. Shi, H. X. Pang, and Z. F. Xie, “PMoA/MCM-41 catalyzed aza-Michael reaction: special effects of mesoporous nanoreactor on chemical equilibrium and reaction rate through surface energy transformation,” New Journal of Chemistry, vol. 39, no. 8, pp. 5916–5919, 2015. View at Publisher · View at Google Scholar · View at Scopus
  22. H. X. Pang, Y. H. Hui, K. Fan et al., “A catalysis study of mesoporous MCM-41 supported Schiff base and CuSO4·5H2O in a highly regioselective synthesis of 4-thiazolidinone derivatives from cyclocondensation of mercaptoacetic acid,” Chinese Chemical Letters, vol. 27, no. 3, pp. 335–339, 2016. View at Publisher · View at Google Scholar · View at Scopus
  23. D. E. Newbury and N. W. M. Ritchie, “Performing elemental microanalysis with high accuracy and high precision by scanning electron microscopy/silicon drift detector energy-dispersive X-ray spectrometry (SEM/SDD-EDS),” Journal of Materials Science, vol. 50, no. 2, pp. 493–518, 2014. View at Publisher · View at Google Scholar · View at Scopus
  24. C. T. Kresge, M. E. Leonowicz, W. J. Roth, J. C. Vartuli, and J. S. Beck, “Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism,” Nature, vol. 359, no. 6397, pp. 710–712, 1992. View at Publisher · View at Google Scholar · View at Scopus
  25. S. H. Chai, H. P. Wang, Y. Liang, and B. Q. Xu, “Sustainable production of acrolein: gas-phase dehydration of glycerol over 12-tungstophosphoric acid supported on ZrO2 and SiO2,” Green Chemistry, vol. 10, no. 10, pp. 1087–1093, 2008. View at Publisher · View at Google Scholar · View at Scopus
  26. S. J. Gharpure and S. K. Nanda, “Stereoselective synthesis of thiazino[4,3-: A] indoles using the thia-Pictet-Spengler reaction of indoles bearing N -tethered thiols and vinylogous thiocarbonates,” Organic & Biomolecular Chemistry, vol. 14, no. 24, pp. 5586–5590, 2016. View at Publisher · View at Google Scholar · View at Scopus