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l-Proline: an efficient catalyst for the synthesis of new spirooxindoles

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Abstract

l-Proline was found to be a versatile organocatalyst for the synthesis of new spirooxindole derivatives in good yields under mild reaction conditions using 1-propanol as a solvent.

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References

  1. Sundberg RJ (1996) The chemistry of indoles. Academic, New York

    Google Scholar 

  2. Da Silva JFM, Garden SJ, Pinto AC (2001) J Braz Chem Soc 12:273

    CAS  Google Scholar 

  3. Abdel-Rahman AH, Keshk EM, Hanna MA, El-Bady SM (2006) Bioorg Med Chem 12:2483

    Article  Google Scholar 

  4. Kang TH, Matsumoto K, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H (2002) Eur J Pharmacol 444:39

    Article  CAS  Google Scholar 

  5. Ma J, Hecht SM (2004) Chem Commun 10:1190

    Article  Google Scholar 

  6. Zhu SL, Ji SJ, Zhang Y (2007) Tetrahedron 63:9365

    Article  CAS  Google Scholar 

  7. Kumar RS, Perumal S (2007) Tetrahedron Lett 48:7164

    Article  Google Scholar 

  8. Redkin RG, Shemchuk LA, Chernykh VP, Shishkin OV, Shishkina SV (2007) Tetrahedron 63:11444

    Article  CAS  Google Scholar 

  9. Shanthi G, Subbulakshmi G, Perumal PT (2007) Tetrahedron 63:2057

    Article  CAS  Google Scholar 

  10. Litviniv YM, Mortikov VY, Shestopalov AM (2008) J Comb Chem 10:741

    Article  Google Scholar 

  11. Wang LM, Jiao N, Qiu J, Yu JJ, Liu JG, Guo FL, Liu Y (2010) Tetrahedron 66:339

    Article  CAS  Google Scholar 

  12. Dabiri M, Bahramnejad M, Baghbanzadeh M (2009) Tetrahedron 65:9443

    Article  CAS  Google Scholar 

  13. Mohammadi AA, Dabiri M, Qaraat M (2009) Tetrahedron 65:3804

    Article  CAS  Google Scholar 

  14. Shanmugam P, Vaithiyanathan V (2009) Tetrahedron 64:3322

    Article  Google Scholar 

  15. Ghandi M, Yari A, Tabatabaei Rezaei SJ, Taheri A (2009) Tetrahedron Lett 50:4724

    Article  CAS  Google Scholar 

  16. Nandakumar A, Thirumurugan P, Perumal PT, Vembu P, Ponnuswamy MN, Ramesh P (2010) Bioorg Med Chem Lett 20:4252

    Article  CAS  Google Scholar 

  17. Chen H, Shi D (2010) J Comb Chem 12:571

    Article  CAS  Google Scholar 

  18. Liu H, Doa G, Shi D (2010) J Comb Chem 12:292

    Article  CAS  Google Scholar 

  19. Alcaide B, Almendros P, Luna A, Torres MS (2006) J Org Chem 71:4818

    Article  CAS  Google Scholar 

  20. Zotova N, Franzke A, Armstrong A, Blackmond DG (2007) J Am Chem Soc 129:15100

    Article  CAS  Google Scholar 

  21. List B, Pojarliev P, Biller WT (2002) J Am Chem Soc 124:827

    Article  CAS  Google Scholar 

  22. Janey JM, Hsiano Y, Armstrong JD (2006) J Org Chem 71:390

    Article  CAS  Google Scholar 

  23. Kantam ML, Rajasekhar CV, Gopikrishna G, Reddy KR, Choudary BM (2006) Tetrahedron Lett 47:5965

    Article  CAS  Google Scholar 

  24. Ramachary DB, Chowdari NS, Barbas CF (2003) Angew Chem 115:4365

    Article  Google Scholar 

  25. Rasalkar MS, Potdar MK, Mohile SS, Salunkhe MM (2005) J Mol Catal A Chem 235:267

    Article  CAS  Google Scholar 

  26. Guo SR, Yuan YQ (2008) Synth Commun 38:2722

    Article  CAS  Google Scholar 

  27. Ramachary DB, Kishore M, Reddy GB (2006) Org Biomol Chem 4:1641

    Article  CAS  Google Scholar 

  28. Ramachary DB, Reddy GB (2006) Org Biomol Chem 4:4463

    Article  CAS  Google Scholar 

  29. Ramachary DB, Kishore M (2007) J Org Chem 72:5056

    Article  CAS  Google Scholar 

  30. Ramachary DB, Ramakumar K, Narayana VV (2007) J Org Chem 72:1458

    Article  CAS  Google Scholar 

  31. Ramachary DB, Kishore M, Reddy YV (2008) Eur J Org Chem 6:975

    Article  Google Scholar 

  32. Shi CL, Shi DQ, Kim SH, Huang ZB, Ji SJ, Ji M (2008) Tetrahedron 64:2425

    Article  CAS  Google Scholar 

  33. Li Y, Chen H, Shi C, Shi D, Ji S (2010) J Comb Chem 12:231

    Article  CAS  Google Scholar 

  34. Bazgir A, Seyyedhamzeh M, Yasaei Z, Mirzaei P (2007) Tetrahedron Lett 48:8790

    Article  CAS  Google Scholar 

  35. Sayyafi M, Seyyedhamzeh M, Khavasi HR, Bazgir A (2008) Tetrahedron 64:2375

    Article  CAS  Google Scholar 

  36. Dabiri M, Delbari AS, Bazgir A (2007) Synlett 821

  37. Dabiri M, Arvin-Nezhad H, Khavasi HR, Bazgir A (2007) Tetrahedron 63:1770

    Article  CAS  Google Scholar 

  38. Jadidi K, Ghahremanzadeh R, Bazgir A (2009) Tetrahedron 65:2005

    Article  CAS  Google Scholar 

  39. Dabiri M, Azimi SC, Khavasi HR, Bazgir A (2008) Tetrahedron 64:7307

    Article  CAS  Google Scholar 

  40. Ghahremanzadeh R, Sayyafi M, Ahadi S, Bazgir A (2009) J Comb Chem 11:393

    Article  CAS  Google Scholar 

  41. Jadidi K, Ghahremanzadeh R, Bazgir A (2009) J Comb Chem 11:341

    Article  CAS  Google Scholar 

  42. Ghahremanzadeh R, Imani Shakibaei G, Ahadi S, Bazgir A (2010) J Comb Chem 12:191

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Islamic Azad University, Karaj Branch, Tehran, Iran

    Afshin Rajabi Khorrami & Parvin Kiani

  2. Department of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran

    Ayoob Bazgir

Authors
  1. Afshin Rajabi Khorrami
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  2. Parvin Kiani
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  3. Ayoob Bazgir
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Correspondence to Ayoob Bazgir.

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Khorrami, A.R., Kiani, P. & Bazgir, A. l-Proline: an efficient catalyst for the synthesis of new spirooxindoles. Monatsh Chem 142, 287–295 (2011). https://doi.org/10.1007/s00706-011-0446-1

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  • DOI: https://doi.org/10.1007/s00706-011-0446-1

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