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

doi:10.1016/S1872-2067(14)60307-7

催化学报 ›› 2015, Vol. 36 ›› Issue (5): 728-733.DOI: 10.1016/S1872-2067(14)60307-7

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

Nanotechnology & Catalysis Research Centre, NANOCAT, University Malaya, Kuala Lumpur, Malaysia

收稿日期:2015-01-07 修回日期:2015-01-29 出版日期:2015-04-17 发布日期:2015-04-17
通讯作者: Nader Ghaffari Khaligh

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

Nanotechnology & Catalysis Research Centre, NANOCAT, University Malaya, Kuala Lumpur, Malaysia

Received:2015-01-07 Revised:2015-01-29 Online:2015-04-17 Published:2015-04-17
Contact: Nader Ghaffari Khaligh

摘要/Abstract

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.

关键词: Brö, nsted acid, Pyrano[4,3-b]pyran, 4-Hydroxy-6-methylpyran-2-one, Three-component reaction, One-pot condensation

Abstract:

Key words: Brö, nsted acid, Pyrano[4,3-b]pyran, 4-Hydroxy-6-methylpyran-2-one, Three-component reaction, One-pot condensation

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.

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参考文献

[1] De Clercq E. Farmaco, 1999, 54: 26
[2] Parreira R L T, Abrahão O, Galembeck S E. Tetrahedron, 2001, 57: 3243
[3] Presti E L, Boggia R, Feltrin A, Menozzi G, Dorigo P, Mosti L. Farmaco, 1999, 54: 465
[4] Anderson W K, Dean D C, Endo T. J Med Chem, 1990, 33: 1667
[5] Rajguru D, Keshwal B S, Jain S. Med Chem Res, 2013, 22: 5934
[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] 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] 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] 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] 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] Tatsuta K, Yamaguchi T, Tsuda Y, Yamaguchi Y, Hattori N, Nagai H, Hosokawa S. Tetrahedron Lett, 2007, 48: 4187
[12] Tanabe K, Hölderich W F. Appl Catal A, 1999, 181: 399
[13] Cole-Hamilton D J. Science, 2003, 299: 1702
[14] Chakrabarti A, Sharma M M. React Polym, 1993, 20: 1
[15] Riego J M, Sedin Z, Zaldivar J M, Marziano N C, Tortato C. Tetrahedron Lett, 1996, 37: 513
[16] Turro N J. Tetrahedron, 1987, 43: 1589
[17] Zolfigol M A, Chehardoli G, Dehghanian M, Niknam K, Shirini F, Khoramabadi-Zad A. J Chin Chem Soc, 2008, 55: 885
[18] Weber U S, Steffen B, Siegers C P. Res Commun Mol Pathol Pharmacol, 1998, 99: 193
[19] Du B X, Yin M Y, Zhang M M, Li Y L, Wang X S. J Heterocycl Chem, 2012, 49: 1439
[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] Anastas P T, Warner J C. Green Chemistry: Theory and Practice. Oxford: Oxford Univ Press, 1998
[22] Mason T J. Ultrason Sonochem, 2007, 14: 476
[23] Khaligh N G, Shirini F. Ultrason Sonochem, 2013, 20: 26
[24] Khaligh N G. Ultrason Sonochem, 2013, 20: 1062
[25] Cravotto G, Cintas P. Chem Soc Rev, 2006, 35: 180
[26] Xia M, Lu Y D. Ultrason Sonochem, 2007, 14: 235
[27] Shirini F, Khaligh N G. Phosphorus Sulfur Silicon Relat Elem, 2011, 186: 2156
[28] Shirini F, Khaligh N G. Dyes Pigm, 2012, 95: 789
[29] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 695
[30] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 1890
[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] Mason T J, Peters D. Practical Sonochemistry: Power Ultrasound Uses and Applications. 2nd Ed. Chichester: Horwood Publishing, 2002. 17
[33] Luche J L. Synthetic Organic Sonochemistry. New York: Plenum Press, 1998
[34] Jin T S, Sun G, Li Y W, Li T S. Green Chem, 2002, 4: 255
[35] Piao M Z, Imafuku K. Tetrahedron Lett, 1997, 38: 5301
[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] Stoyanov E V, Ivanov I C, Heber D. Molecules, 2000, 5: 19
[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] Wang X S, Zeng Z S, Li Y L, Shi D Q, Tu S J, Zhou J X. Arkivoc, 2006, (11): 107
[40] Shaabani A, Samadi S, Badri Z, Rahmati A. Catal Lett, 2005, 104: 39
[41] Shaabani A, Samadi S, Rahmati A. Synth Commun, 2007, 37: 491
[42] Seifi M, Sheibani H. Catal Lett, 2008, 126: 275
[43] Rajguru D, Keshwal B S, Jain S. Chin Chem Lett, 2013, 24: 1033
[44] Khaligh N G. Monatsh Chem, 2014, 145: 1643
[45] Ghashang M, Mansoor S S, Aswin K. Chin J Catal (催化学报), 2014, 35: 127

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

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

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