Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Saccharin Sulfonic Acid as an Efficient Catalyst for the Preparation and Deprotection of 1,1-Diacetates

  • Shirini, F. (Department of Chemistry, College of Science, University of Guilan) ;
  • Mamaghani, M. (Department of Chemistry, College of Science, University of Guilan) ;
  • Mostashari-Rad, T. (Department of Chemistry, College of Science, University of Guilan) ;
  • Abedini, M. (Department of Chemistry, College of Science, University of Guilan)
  • Received : 2010.05.30
  • Accepted : 2010.06.24
  • Published : 2010.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Greene, T. W.; Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 4th ed.; Wiley: New York, 2007..
  2. Kochhar, K. S.; Bal, B. S.; Deshpande, R. P.; Rajadhyaksha, S. N.; Pinnick, H. W. J. Org. Chem. 1983, 48, 1765. https://doi.org/10.1021/jo00158a036
  3. Trost, B. M.; Lee, C. J. Am. Chem. Soc. 2001, 123, 12191. https://doi.org/10.1021/ja0118338
  4. Sandberg, M.; Sydnes, L. K. Org. Lett. 2000, 2, 687. https://doi.org/10.1021/ol005535b
  5. Held, H.; Rengestle, A.; Mayer, A. In Ullman's Encyclopedia of Industrial Chemistry, 5 th ed.; Gerhartz, W., Ed.; Wiley-VCH: New York, 1985; Vol. 1.
  6. Freeman, F.; Karchefski, E. M. J. Chem. Eng. Data 1977, 22, 355. https://doi.org/10.1021/je60074a038
  7. Frick, J. G., Jr. ; Harper, R. J., Jr. J. Appl. Polym. Sci. 1984, 29, 1433. https://doi.org/10.1002/app.1984.070290436
  8. Eanderson, W. R. Eur. Pat. Appl. 1985, EP 125 781
  9. Eanderson, W. R. Chem. Abstr. 1985, 102, P64010K.
  10. Van Heerden, F. R.; Huyser, J. J.; Bradley, D.; Williams, G.; Holzapfel, C. W. Tetrahedron Lett. 1988, 39, 5281.
  11. Sandberg, M.; Sydnes, L. K. Tetrahedron Lett. 1998, 39, 6361. https://doi.org/10.1016/S0040-4039(98)01309-4
  12. Manjula, K.; Afzal Pasha, M. Synth. Commun. 2007, 37, 1563. https://doi.org/10.1080/00397910701239015
  13. Desai, U. V.; Thopate, T. S.; Pore, D. M.; Wadgaonkar, P. P. Catal. Commun. 2006, 7, 508. https://doi.org/10.1016/j.catcom.2005.12.028
  14. Wang, M.; Gong, H.; Jiang, H.; Wang, Z. Synth. Commun. 2006, 36, 1953. https://doi.org/10.1080/00397910600633979
  15. Gregory, M. J. J. Chem. Soc. B 1970, 1201. https://doi.org/10.1039/j29700001201
  16. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F.; Amani, K. Tetrahedron Lett. 2003, 44, 3951. https://doi.org/10.1016/S0040-4039(03)00811-6
  17. Nagy, N. M.; Jakab, M. A.; Konya, J.; Antus, S. Appl. Clay Sci. 2002, 21, 213. https://doi.org/10.1016/S0169-1317(02)00066-2
  18. Smitha, G.; Reddy, C. S. Tetrahedron 2003, 59, 9571. https://doi.org/10.1016/j.tet.2003.10.002
  19. Wang, J.; Yan, L.; Qian, G.; Yang, K.; Liu, H.; Wang, X. Tetrahedron Lett. 2006, 47, 8309. https://doi.org/10.1016/j.tetlet.2006.09.090
  20. Kumar, R.; Tiwari, P.; Maulik, P. R.; Misra, A. K. J. Mol. Catal. A: Chem. 2006, 247, 27. https://doi.org/10.1016/j.molcata.2005.11.019
  21. Jeyakumar, K.; Chand, D. K. J. Mol. Catal. A: Chem. 2006, 255, 275. https://doi.org/10.1016/j.molcata.2006.04.026
  22. Wang, M.; Song, Z.; Gong, H.; Jiang, H. Synth. Commun. 2008, 38, 961. https://doi.org/10.1080/00397910701845720
  23. Saini, A.; Kumar, S.; Sandhu, J. S. Synth. Commun. 2008, 38, 106. https://doi.org/10.1080/00397910701650831
  24. Khan, A. T.; Choudhury, L. H.; Ghosh, S. J. Mol. Catal. A: Chem. 2006, 255, 230. https://doi.org/10.1016/j.molcata.2006.04.008
  25. Aggen, D. H.; Arnold, J. N.; Hayes, P. D.; Smoter, N. J.; Mohan, R. S. Tetrahedron 2004, 60, 3675. https://doi.org/10.1016/j.tet.2004.02.046
  26. Kolvari, E.; Ghorbani-Choghamarani, A.; Salehi, P.; Shirini, F.; Zolfigol, M. A. J. Iran. Chem. Soc. 2007, 2, 126.
  27. Shirini, F.; Zolfigol, M. A.; Salehi, P.; Abedini, M. Current Org. Chem. 2008, 12, 183. https://doi.org/10.2174/138527208783497475
  28. Shirini, F.; Abedini, M.; Ghasemi, M.; Sakhaei, A. R. Bull. Korean Chem. Soc. 2009, 10, 2479.
  29. Shirini, F.; Zolfigol, M. A.; Albadi, J. Synth. Commun. 2010, 40, 910. https://doi.org/10.1080/00397910903026707
  30. Shirini, F.; Zolfigol, M. A.; Abedini, M. Monatsh. Chem. 2009, 140, 61. https://doi.org/10.1007/s00706-008-0004-7
  31. Shirini, F.; Zolfigol, M. A.; Abedini, M. Monatsh. Chem. 2009, 140, 1495. https://doi.org/10.1007/s00706-009-0214-7

Cited by

  1. Iranian chemist’s efforts to provide various effective methods for the synthesis of xanthenes vol.11, pp.3, 2014, https://doi.org/10.1007/s13738-013-0353-y
  2. -Diacetates from Aldehydes vol.61, pp.8, 2014, https://doi.org/10.1002/jccs.201400049
  3. Microwave-assisted green synthesis of 1,1-diacetates (acylals) using selectfluor™ as an environmental-friendly catalyst under solvent-free conditions vol.42, pp.3, 2016, https://doi.org/10.1007/s11164-015-2168-1
  4. Synthesis of sulfonated carbon-based solid acid as a novel and efficient nanocatalyst for the preparation of highly functionalized piperidines and acylals: a DFT study vol.42, pp.6, 2016, https://doi.org/10.1007/s11164-016-2448-4
  5. N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) as a green and reusable heterogeneous nanocatalyst for the chemoselective preparation and deprotection of acylals vol.43, pp.11, 2017, https://doi.org/10.1007/s11164-017-3014-4
  6. ChemInform Abstract: Saccharin Sulfonic Acid as an Efficient Catalyst for the Preparation and Deprotection of 1,1‐Diacetates. vol.41, pp.50, 2010, https://doi.org/10.1002/chin.201050057
  7. Saccharin Sulfonic Acid (SASA) as a Highly Efficient Catalyst for the Condensation of 2-Naphthol With Arylaldehydes and Amides (Thioamides or Alkyl Carbamates) Under Green, Mild, and Solvent-Free Cond vol.188, pp.5, 2010, https://doi.org/10.1080/10426507.2012.692131
  8. Introduction of taurine (2-aminoethanesulfonic acid) as a green bio-organic catalyst for the promotion of organic reactions under green conditions vol.6, pp.111, 2010, https://doi.org/10.1039/c6ra15432h
  9. Novel Carbon-based Solid Acid from Green Pistachio Peel as an Efficient Catalyst for the Chemoselective Acylation, Acetalization and Thioacetalization of Aldehydes, Synthesis of Biscoumarins and Antim vol.7, pp.1, 2019, https://doi.org/10.2174/2213337206666190717164606
  10. Catalytic Applications of Saccharin and its Derivatives in Organic Synthesis vol.23, pp.28, 2020, https://doi.org/10.2174/1385272823666191121144758
  11. Artificial sugar saccharin and its derivatives: role as a catalyst vol.10, pp.60, 2010, https://doi.org/10.1039/d0ra05974a