Citation: Nader Ghaffari Khaligh, Sharifah Bee Abd Hamid. 4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for the synthesis of pyrano[4, 3-b]pyran derivatives using thermal and ultrasonic irradiation[J]. Chinese Journal of Catalysis, ;2015, 36(5): 728-733. doi: 10.1016/S1872-2067(14)60307-7 shu

4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for the synthesis of pyrano[4, 3-b]pyran derivatives using thermal and ultrasonic irradiation

  • Corresponding author: Nader Ghaffari Khaligh, 
  • Received Date: 7 January 2015
    Available Online: 29 January 2015

  • 4-(Succinimido)-1-butane sulfonic acid was shown to be an efficient and reusable Brönsted acid catalyst for the synthesis of pyrano[4,3-b]pyran derivatives using thermal and ultrasonic conditions. The catalyst was prepared by mixing succinimide and 1,4-butanesultone, which is simpler and safer than the preparation of succinimide sulfonic acid. This method has the advantages of high yield, clean reaction, simple methodology, and short reaction time. The catalyst can be recycled without loss of activity.
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    1. [1]

      [1] De Clercq E. Farmaco, 1999, 54: 26

    2. [2]

      [2] Parreira R L T, Abrahão O, Galembeck S E. Tetrahedron, 2001, 57: 3243

    3. [3]

      [3] Presti E L, Boggia R, Feltrin A, Menozzi G, Dorigo P, Mosti L. Farmaco, 1999, 54: 465

    4. [4]

      [4] Anderson W K, Dean D C, Endo T. J Med Chem, 1990, 33: 1667

    5. [5]

      [5] Rajguru D, Keshwal B S, Jain S. Med Chem Res, 2013, 22: 5934

    6. [6]

      [6] Dragovich P S, Prins T J, Zhou R, Brown E L, Maldonado F C, Fuhrman S A, Zalman L S, Tuntland T, Lee C A, Patick A K, Matthews D A, Hendrickson T F, Kosa M B, Liu B, Batugo M R, Gleeson J P R, Sakata S K, Chen L J, Guzman M C, Meador J W III, Ferre R A, Worland S T. J Med Chem, 2002, 45: 1607

    7. [7]

      [7] Kemnitzer W, Kasibhatla S, Jiang S C, Zhang H, Zhao J H, Jia S J, Xu L F, Crogan-Grundy C, Denis R, Barriault N, Vaillancourt L, Charron S, Dodd J, Attardo G, Labrecque D, Lamothe S, Gourdeau H, Tseng B, Drewe J, Cai S X. Bioorg Med Chem Lett, 2005, 15: 4745

    8. [8]

      [8] Kemnitzer W, Drewe J, Jiang S C, Zhang H, Wang Y, Zhao J H, Jia S J, Herich J, Labreque D, Storer R, Meerovitch K, Bouffard D, Rej R, Denis R, Blais C, Lamothe S, Attardo G, Gourdeau H, Tseng B, Kasibhatla S, Cai S X. J Med Chem, 2004, 47: 6299

    9. [9]

      [9] Kemnitzer W, Drewe J, Jiang S C, Zhang H, Zhao J H, Crogan-Grundy C, Xu L F, Lamothe S, Gourdeau H, Denis R, Tseng B, Kasibhatla S, Cai S X. J Med Chem, 2007, 50: 2858

    10. [10]

      [10] Fan X S, Feng D, Qu Y Y, Zhang X Y, Wang J J, Loiseau P M, Andrei G, Snoeck R, Clercq E D. Bioorg Med Chem Lett, 2010, 20: 809

    11. [11]

      [11] Tatsuta K, Yamaguchi T, Tsuda Y, Yamaguchi Y, Hattori N, Nagai H, Hosokawa S. Tetrahedron Lett, 2007, 48: 4187

    12. [12]

      [12] Tanabe K, Hölderich W F. Appl Catal A, 1999, 181: 399

    13. [13]

      [13] Cole-Hamilton D J. Science, 2003, 299: 1702

    14. [14]

      [14] Chakrabarti A, Sharma M M. React Polym, 1993, 20: 1

    15. [15]

      [15] Riego J M, Sedin Z, Zaldivar J M, Marziano N C, Tortato C. Tetrahedron Lett, 1996, 37: 513

    16. [16]

      [16] Turro N J. Tetrahedron, 1987, 43: 1589

    17. [17]

      [17] Zolfigol M A, Chehardoli G, Dehghanian M, Niknam K, Shirini F, Khoramabadi-Zad A. J Chin Chem Soc, 2008, 55: 885

    18. [18]

      [18] Weber U S, Steffen B, Siegers C P. Res Commun Mol Pathol Pharmacol, 1998, 99: 193

    19. [19]

      [19] Du B X, Yin M Y, Zhang M M, Li Y L, Wang X S. J Heterocycl Chem, 2012, 49: 1439

    20. [20]

      [20] Patil A D, Freyer A J, Eggleston D S, Haltiwanger R C, Bean M F, Taylor P B, Caranfa M J, Breen A L, Bartus H R, Johnson R K, Hertzberg R P, Westley J W. J Med Chem, 1993, 36: 4131

    21. [21]

      [21] Anastas P T, Warner J C. Green Chemistry: Theory and Practice. Oxford: Oxford Univ Press, 1998

    22. [22]

      [22] Mason T J. Ultrason Sonochem, 2007, 14: 476

    23. [23]

      [23] Khaligh N G, Shirini F. Ultrason Sonochem, 2013, 20: 26

    24. [24]

      [24] Khaligh N G. Ultrason Sonochem, 2013, 20: 1062

    25. [25]

      [25] Cravotto G, Cintas P. Chem Soc Rev, 2006, 35: 180

    26. [26]

      [26] Xia M, Lu Y D. Ultrason Sonochem, 2007, 14: 235

    27. [27]

      [27] Shirini F, Khaligh N G. Phosphorus Sulfur Silicon Relat Elem, 2011, 186: 2156

    28. [28]

      [28] Shirini F, Khaligh N G. Dyes Pigm, 2012, 95: 789

    29. [29]

      [29] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 695

    30. [30]

      [30] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 1890

    31. [31]

      [31] Suslick K S, Didenko Y, Fang M M, Hyeon T, Kolbeck K J, McNamara W B III, Mdleleni M M, Wong M. Philos Trans R Soc A, 1999, 357: 335

    32. [32]

      [32] Mason T J, Peters D. Practical Sonochemistry: Power Ultrasound Uses and Applications. 2nd Ed. Chichester: Horwood Publishing, 2002. 17

    33. [33]

      [33] Luche J L. Synthetic Organic Sonochemistry. New York: Plenum Press, 1998

    34. [34]

      [34] Jin T S, Sun G, Li Y W, Li T S. Green Chem, 2002, 4: 255

    35. [35]

      [35] Piao M Z, Imafuku K. Tetrahedron Lett, 1997, 38: 5301

    36. [36]

      [36] Magedov I V, Manpadi M, Ogasawara M A, Dhawan A S, Rogelj S, Van Slambrouck S, Steelant W F A, Evdokimov N M, Uglinskii P Y, Elias E M, Knee E J, Tongwa P, Antipin M Y, Kornienko A. J Med Chem, 2008, 51: 2561

    37. [37]

      [37] Stoyanov E V, Ivanov I C, Heber D. Molecules, 2000, 5: 19

    38. [38]

      [38] Shi D Q, Niu L H, Zhuang Q Y. Chin J Org Chem (史达清, 牛力惠, 庄启亚. 有机化学), 2008, 28: 1633

    39. [39]

      [39] Wang X S, Zeng Z S, Li Y L, Shi D Q, Tu S J, Zhou J X. Arkivoc, 2006, (11): 107

    40. [40]

      [40] Shaabani A, Samadi S, Badri Z, Rahmati A. Catal Lett, 2005, 104: 39

    41. [41]

      [41] Shaabani A, Samadi S, Rahmati A. Synth Commun, 2007, 37: 491

    42. [42]

      [42] Seifi M, Sheibani H. Catal Lett, 2008, 126: 275

    43. [43]

      [43] Rajguru D, Keshwal B S, Jain S. Chin Chem Lett, 2013, 24: 1033

    44. [44]

      [44] Khaligh N G. Monatsh Chem, 2014, 145: 1643

    45. [45]

      [45] Ghashang M, Mansoor S S, Aswin K. Chin J Catal (催化学报), 2014, 35: 127

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