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An environmentally friendly approach for the synthesis of quinazolinone sulfonamide

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Abstract

An efficient synthesis of quinazolinone sulfonamide derivatives through four-component reaction is reported. The four-component reaction is based on the reaction of isatoic anhydride, hydrazine hydrate, saccharin, and aromatic aldehydes in the presence of nano-catalyst SBA-Pr-SO3H. Saccharin was used as a novel source of sulfonamide moiety in this reaction.

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References

  1. Ugi I, Dömling A, Hörl W (1994) Endeavour 18:115

    Article  CAS  Google Scholar 

  2. Armstrong RM, Combs AP, Tempest PA, Brown SD, Keating TA (1996) Acc Chem Res 29:123

    Article  CAS  Google Scholar 

  3. Bienaymé H, Hulme C, Oddon G, Schmitt P (2000) Chem Eur J 6:3321

    Article  Google Scholar 

  4. Harmer MA (2002) In: Clark JH, Macquarrie DJ (eds) Handbook of green chemistry & technology. Blackwell, Oxford

    Google Scholar 

  5. Clark JH (2002) Acc Chem Res 35:791

    Article  CAS  Google Scholar 

  6. Wilson K, Adams DJ, Rothenberg G, Clark JH (2000) J Mol Catal A Chem 159:309

    Article  CAS  Google Scholar 

  7. Wight AP, Davis ME (2002) Chem Rev 102:3589

    Article  CAS  Google Scholar 

  8. Lim MH, Blanford CF, Stein A (1998) Chem Mater 10:467

    Article  CAS  Google Scholar 

  9. Fathi Vavsari V, Mohammadi Ziarani G, Badiei A (2015) RSC Adv 5:91686

    Article  CAS  Google Scholar 

  10. Karimi B, Vafaeezadeh M (2012) Chem Commun 48:3327

    Article  CAS  Google Scholar 

  11. VanGrieken R, Melero JA, Morales G (2005) Appl Catal A 289:143

    Article  CAS  Google Scholar 

  12. Fathi Vavsari V, Mohammadi Ziarani G, Badiei A, Balalaie S (2016) J Iran Chem Soc 13:1037

    Article  CAS  Google Scholar 

  13. Xue S, McKenna J, Shieh WC, Repic O (2004) J Org Chem 69:6474

    Article  CAS  Google Scholar 

  14. Honkanen E, Pippuri A, Kairisalo P, Nore P, Karppanen H, Paakkari I (1983) J Med Chem 26:1433

    Article  CAS  Google Scholar 

  15. Zhou Y, Murphy DE, Sun Z, Gregor VE (2004) Tetrahedron Lett 45:8049

    Article  CAS  Google Scholar 

  16. Panneerselvam P, Pradeepchandran RV, Sridhar SK (2003) Ind J Pharm Sci 65:268

    CAS  Google Scholar 

  17. Refaie FM, Esmat AY, Gawad SMA, Ibrahim AM, Mohamed MA (2005) Lipids Health Dis 4:1

    Article  Google Scholar 

  18. Habib NS, Ismail KA, El-Tombary AA, Abdel AT (2000) Pharmazie 55:495

    CAS  Google Scholar 

  19. Jessy EM, Sambanthan AT, Alex J, Sridevi CH, Srinivasan KK (2007) Ind J Pharm Sci 69:476

    Article  CAS  Google Scholar 

  20. Alagarsamy V, Solomon VR, Dhanabal K (2007) Bioorg Med Chem 15:235

    Article  CAS  Google Scholar 

  21. Georgey H, Abdel-Gawad N, Abbas S (2008) Molecules 13:2557

    Article  CAS  Google Scholar 

  22. Guan LP, Jin QH, Tian GR, Chai KY, Quan ZS (2007) J Pharm Pharm Sci 10:254

    CAS  Google Scholar 

  23. El-Azab AS, Abdel-Hamide SG, Sayed-Ahmed MM, Hassan GS, El-Hadiyah TM, Al-Shabanah OA, Al-Deeb OA, El-Subbagh HI (2013) Med Chem Res 22:2815

    Article  CAS  Google Scholar 

  24. Malawska B (2005) Curr Top Med Chem 5:69

    Article  CAS  Google Scholar 

  25. Srivastava VK, Kumar A (2004) Bioorg Med Chem 12:1257

    Article  Google Scholar 

  26. Li J, Meng Y, Liu Y, Feng ZQ, Chen XG (2010) Invest New Drugs 28:132

    Article  CAS  Google Scholar 

  27. Chandrika PM, Yakaiah T, Rao ARR, Narsaiah B, Reddy NC, Sridhar V, Rao JV (2008) Eur J Med Chem 43:846

    Article  CAS  Google Scholar 

  28. Foote KM, Mortlock AA, Heron NM, Jung FH, Hill GB, Pasquet G, Brady MC, Green S, Heaton SP, Kearney S, Keen NJ (2008) Bioorg Med Chem Lett 18:1904

    Article  CAS  Google Scholar 

  29. Cao SL, Feng YP, Jiang YY, Liu SY, Ding GY, Li RT (2005) Bioorg Med Chem Lett 15:1915

    Article  CAS  Google Scholar 

  30. Al-Omary FA, Abou-Zeid LA, Nagi MN, Habib ESE, Alaa AM, El-Azab AS, Abdel-Hamide SG, Al-Omar MA, Al-Obaid AM, El-Subbagh HI (2010) Bioorg Med Chem 18:2849

    Article  CAS  Google Scholar 

  31. Kołazzek A, Fusiarz I, Ławeccka J, Branowska D (2014) Chemik 68:620

    Google Scholar 

  32. Kataoka T, Iwama T, Setta T, Takagi A (1998) Synthesis 4:423

    Article  Google Scholar 

  33. Deng X, Mani N (2006) Green Chem 8:835

    Article  CAS  Google Scholar 

  34. Shi F, Kin Tse M, Zhou S, Pohl MM, Radnik J, Huebner S, Jaehnlisch K, Brueckner A, Beller M (2009) J Am Chem Soc 131:1775

    Article  CAS  Google Scholar 

  35. Massah AR, Sayadi S, Ebrahimi S (2012) RSC Adv 2:6606

    Article  Google Scholar 

  36. Bahrami K, Khodaei M, Soheilizad M (2009) J Org Chem 74:9287

    Article  CAS  Google Scholar 

  37. Masereel B, Rolin S, Francesco Abbate F, Scozzafava A, Supuran CT (2002) J Med Chem 45:312

    Article  CAS  Google Scholar 

  38. Reddy NS, Reddy MM, Cosenza S, Gumireddy K (2004) Bioorg Med Chem Lett 14:4093

    Article  CAS  Google Scholar 

  39. Li XH, Yang XL, Ling Y, Fan ZJ, Liang XM, Wang DQ, Chen FH, Li ZM (2005) J Agric Food Chem 53:2202

    Article  CAS  Google Scholar 

  40. Hu L, Li ZR, Li Y, Qu J, Ling YH, Jiang JD, Boykin DW (2006) J Med Chem 49:6273

    Article  CAS  Google Scholar 

  41. Accinelli C, Koskinen WC, Becker JM, Sadowsky MJ (2007) J Agric Food Chem 55:2677

    Article  CAS  Google Scholar 

  42. Ghorab MM, Ismail ZH, Radwan AA, Abdalla M (2013) Acta Pharm 63:1

    Article  CAS  Google Scholar 

  43. Abbate F, Casini A, Owa T, Scozzafava A, Supuran CT (2004) Bioorg Med Chem Lett 14:217

    Article  CAS  Google Scholar 

  44. Hayun, Yanuar A, Hanafi M, Hudiyono PWS (2011) Bioinformation 7:246

    Article  CAS  Google Scholar 

  45. Vanparia SF, Patel TS, Dixit RB, Dixit BC (2013) Med Chem Res 22:5184

    Article  CAS  Google Scholar 

  46. Maarouf AR, El-Bendary ER, Goda FE (2004) Arch Pharm Pharm Med Chem 337:527

    Article  CAS  Google Scholar 

  47. Ghorab MM, Alsaid MS, Al-Dosari MS, El-Gazzar MG, Parvez MK (2016) Molecules 21:189

    Article  Google Scholar 

  48. Al-Rashood ST, Aboldahab IA, Nagi MN, Abouzeid LA, Abdel-Aziz AAM, Abdel-hamide SG, Youssef KM, Al-Obaida AM, El-Subbagh HI (2006) Bioorg Med Chem 14:8608

    Article  CAS  Google Scholar 

  49. Zhou Y, Murphy DE, Sun Z, Gregor VE (2004) Tetrahedron Lett 45:8049

    Article  CAS  Google Scholar 

  50. Smirnov GA, Sizova EP, Lukyanov OA, Fedyanin IV, Antipin MY (2003) Russ Chem Bull 52:2444

    Article  CAS  Google Scholar 

  51. Ding QS, Zhang JX, Liu MC, Ding JC, Wu HY (2012) J Heterocycl Chem 49:375

    Article  CAS  Google Scholar 

  52. Ibrahim SM, Baraka MM, El-Sabbagh OI, Kothayer H (2013) Med Chem Res 22:1488

    Article  CAS  Google Scholar 

  53. Agar DJ, Pantaleone DP, Henderson SA, Katritzky AR, Prakash I, Walters DE (1998) Angew Chem Int Ed 37:1802

    Article  Google Scholar 

  54. Balalaie S, Bijanzadeh HR, Mehrparvar S, Rominger F (2016) Synlett 27:782

    Article  CAS  Google Scholar 

  55. Balalaie S, Ramezanpour S (2016) Helv Chim Acta 99:138

    Article  CAS  Google Scholar 

  56. Fathi V, Ramezanpour S, Balalaie S, Rominger F, Bijanzadeh H (2014) Helv Chim Acta 97:1630

    Article  CAS  Google Scholar 

  57. Nikbakht A, Ramezanpour S, Balalaie S, Rominger F (2015) Tetrahedron 71:6790

    Article  CAS  Google Scholar 

  58. Alavijeh NS, Zadmard R, Ramezanpour S, Balalaie S, Alavijeh MS, Rominger F (2015) New J Chem 39:6578

    Article  CAS  Google Scholar 

  59. Maghari S, Ramezanpour S, Balalaie S, Darvish F, Rominger F, Bijanzadeh HR (2013) J Org Chem 78:6450

    Article  CAS  Google Scholar 

  60. Ahadi S, Naghdiani Z, Balalaie S, Rominger F (2015) Tetrahedron 71:6860

    Article  CAS  Google Scholar 

  61. Tajbakhsh M, Ramezanpour S, Balalaie S, Bijanzadeh HR (2015) J Heterocycl Chem 52:1559

    Article  CAS  Google Scholar 

  62. Mehrparvar S, Balalaie S, Rabbanizadeh M, Rominger F, Ghabraie E (2014) Org Biomol Chem 12:5757

    Article  CAS  Google Scholar 

  63. Ghabraie E, Balalaie S, Mehrparvar S, Rominger F (2014) J Org Chem 79:7926

    Article  CAS  Google Scholar 

  64. Fathi Vavsari V, Dianati V, Ramezanpour S, Balalaie S (2015) Synlett 26:1955

    Article  Google Scholar 

  65. Sheldrick GM (2012) Bruker analytical X-ray division. Madison, Wisconsin

    Google Scholar 

  66. Sheldrick GM (2015) Acta Cryst C71:3

    Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the Iran National Science Foundation (INSF) for the financial support.

Author information

Authors and Affiliations

  1. Peptide Chemistry Research Center, K.N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran

    Saeed Balalaie, Sorour Ramezanpour & Vaezeh Fathi Vavsari

  2. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Saeed Balalaie

  3. Department of Chemistry, North Branch of Tehran, Islamic Azad University, Tehran, Iran

    Shohreh Hekmat & Hasan Kabiri-Fard

  4. Organisch-Chemisches Institut der Universitat Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany

    Frank Rominger

Authors
  1. Saeed Balalaie
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  2. Shohreh Hekmat
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  3. Sorour Ramezanpour
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  4. Frank Rominger
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  5. Hasan Kabiri-Fard
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  6. Vaezeh Fathi Vavsari
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Corresponding author

Correspondence to Saeed Balalaie.

Additional information

Dedicated to Prof. Ali Pourjavadi on the occasion of his 65th birthday.

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Balalaie, S., Hekmat, S., Ramezanpour, S. et al. An environmentally friendly approach for the synthesis of quinazolinone sulfonamide. Monatsh Chem 148, 1453–1461 (2017). https://doi.org/10.1007/s00706-017-1924-x

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  • DOI: https://doi.org/10.1007/s00706-017-1924-x

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