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

Nader Ghaffari Khaligh Sharifah Bee Abd Hamid

引用本文: 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]. 催化学报, 2015, 36(5): 728-733. doi: 10.1016/S1872-2067(14)60307-7 shu
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

    通讯作者: Nader Ghaffari Khaligh
摘要: 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.

English

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    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[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] Wang X S, Zeng Z S, Li Y L, Shi D Q, Tu S J, Zhou J X. Arkivoc, 2006, (11): 107[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] Shaabani A, Samadi S, Badri Z, Rahmati A. Catal Lett, 2005, 104: 39[40] Shaabani A, Samadi S, Badri Z, Rahmati A. Catal Lett, 2005, 104: 39

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

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

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

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

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

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  1094
  • HTML全文浏览量:  62
文章相关
  • 发布日期:  2015-05-20
  • 收稿日期:  2015-01-07
  • 网络出版日期:  2015-01-29
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章