Skip to main content
SpringerLink
Log in

Synthesis of spirooxindole pyrimidines catalyzed by silica-bonded N-propyltriethylenetetramine as a recyclable solid base catalyst in aqueous medium

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Silica-bonded N-propyltriethylenetetramine was used as a heterogeneous solid base catalyst for the synthesis of spirooxindole pyrimidines by a one-pot condensation reaction of isatin, activated methylene reagent, and barbituric acid or thiobarbituric acid in aqueous medium in good to high yields. Catalyst could be recycled for several times without any additional treatment.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Cheng D, Ishihara Y, Tan B, Barbas CF (2014) ACS Catal 4:743

    Article  CAS  Google Scholar 

  2. Ding K, Lu YP, Coleska N (2006) J Med Chem 49:3432

    Article  CAS  Google Scholar 

  3. Galliford CV, Scheidt KA (2007) Angew Chem Int Ed 46:8748

    Article  CAS  Google Scholar 

  4. Chai SJ, Lai YF, Xu JC, Zheng H, Zhu Q, Zhang PF (2011) Adv Synth Catal 353:371

    Article  CAS  Google Scholar 

  5. Galliford CV, Martenson JA, Stern C, Scheidt KA (2007) Chem Commun 631

  6. Cui CB, Kakeya H, Osada H (1996) Tetrahedron 52:12651

    Article  CAS  Google Scholar 

  7. Cui CB, Kakeya H, Osada H (1996) J Antibiot 49:832

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  9. Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B (1991) J Org Chem 56:6527

    Article  CAS  Google Scholar 

  10. Anderton N, Cockrum PA, Colegate SM, Edgar JA, Flower K, Vit I, Willing RI (1998) Phytochemistry 48:437

    Article  CAS  Google Scholar 

  11. Dideberg O, Lamotte-Brasseur J, Dupont L, Campsteyn H, Vermeire M, Angenot L (1977) Acta Crystallogr Sect B 33:1796

    Article  Google Scholar 

  12. Elderfield RC, Gilman RE (1972) Phytochemistry 11:339

    Article  CAS  Google Scholar 

  13. Ghedira K, Zeches-Hanrot M, Richard B, Massiot G, Le Men-Oliver L, Sevener T, Goh SH (1988) Phytochemistry 27:3955

    Article  CAS  Google Scholar 

  14. Wong WH, Lim PB, Chuah CH (1996) Phytochemistry 41:313

    Article  CAS  Google Scholar 

  15. Garnick RL, Le Quesne PW (1978) J Am Chem Soc 100:4213

    Article  CAS  Google Scholar 

  16. Sakai S, Aimi N, Yamaguchi K, Ohhira H, Hori K, Haginiwa J (1975) Tetrahedron Lett 16:715

    Article  Google Scholar 

  17. Aimi N, Yamaguchi K, Sakai S, Haginiwa J, Kubo A (1978) Chem Pharm Bull 26:3444

    Article  CAS  Google Scholar 

  18. Sakai S, Aimi N, Yamaguchi K, Yamanaka E, Haginiwa J (1982) J Chem Soc Perkin Trans 1:1257

    Article  Google Scholar 

  19. Edmondson S, Danishefsky SJ, Sepp-Lorenzino L, Rosen N (1999) J Am Chem Soc 121:2147

    Article  CAS  Google Scholar 

  20. Edmonson SD, Danishefsky SJ (1998) Angew Chem Int Ed 37:1138

    Article  Google Scholar 

  21. Wang HS, Ganesan A (1997) Tetrahedron Lett 38:4327

    Article  CAS  Google Scholar 

  22. Wang HS, Ganesan A (2000) J Org Chem 65:4685

    Article  CAS  Google Scholar 

  23. Miyake FY, Yakushijin K, Horne DA (2004) Org Lett 6:711

    Article  CAS  Google Scholar 

  24. Miyake FY, Yakushijin K, Horne DA (2004) Angew Chem Int Ed 43:5357

    Article  CAS  Google Scholar 

  25. Baran PS, Richter JM (2005) J Am Chem Soc 127:15394

    Article  CAS  Google Scholar 

  26. Baran PS, Maimone TJ, Richter JM (2007) Nature 446:404

    Article  CAS  Google Scholar 

  27. Fuji K, Kawabata T, Ohmori T, Node M (1995) Synlett 367

  28. Fuji K, Node M, Nagasawa H, Naniwa Y, Taga T, Machida K, Snatzke G (1989) J Am Chem Soc 111:7921

    Article  CAS  Google Scholar 

  29. Overman LE, Peterson EA (2003) Tetrahedron 59:6905

    Article  CAS  Google Scholar 

  30. Matsuura T, Overman LE, Poon DJ (1998) J Am Chem Soc 120:6500

    Article  CAS  Google Scholar 

  31. Huang A, Kodanko JJ, Overman LE (2004) J Am Chem Soc 126:14043

    Article  CAS  Google Scholar 

  32. Overman LE, Rosen MD (2000) Angew Chem Int Ed 39:4596

    Article  CAS  Google Scholar 

  33. Trost BM, Stambuli JP, Silverman SM, Schworer U (2006) J Am Chem Soc 128:13328

    Article  CAS  Google Scholar 

  34. Trost BM, Cramer N, Silverman SM (2007) J Am Chem Soc 129:12396

    Article  CAS  Google Scholar 

  35. Trost BM, Brennan MK (2009) Synthesis 3003

  36. Meyers C, Carreira EM (2003) Angew Chem 115:718

    Article  Google Scholar 

  37. Marti C, Carreira EM (2005) J Am Chem Soc 127:11505

    Article  CAS  Google Scholar 

  38. Wuitschik G, Rogers-Evans M, Buckl A, Bernasconi M, Marki M, Godel T, Fischer H, Wagner B, Parrilla I, Schuler F, Schneider J, Alker A, Schweizer WB, Muller K, Carreira EM (2008) Angew Chem Int Ed 47:4512

    Article  CAS  Google Scholar 

  39. Sebahar PR, Williams RM (2000) J Am Chem Soc 122:5666

    Article  CAS  Google Scholar 

  40. Onishi T, Sebahar PR, Williams RM (2003) Org Lett 5:3135

    Article  CAS  Google Scholar 

  41. Williams RM, Cao J, Tsujishima H, Cox RJ (2003) J Am Chem Soc 125:12172

    Article  CAS  Google Scholar 

  42. Chen XH, Wei Q, Luo SW, Xiao H, Gong LZ (2009) J Am Chem Soc 131:13819

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  44. Elinson MN, Ilovaisky AI, Dorofeev AS, Merkulova VM, Stepanov NO, Miloserdov FM, Ogibin YN, Nikishin GI (2007) Tetrahedron 63:10543

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  47. Gao S, Tsai CH, Tseng C, Yao CF (2008) Tetrahedron 64:9143

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. Dandia A, Parewa V, Jain AK, Rathore KS (2011) Green Chem 13:2135

    Article  CAS  Google Scholar 

  51. Dandia A, Jain AK, Bhati DS (2011) Synth Commun 41:2905

    Article  CAS  Google Scholar 

  52. Rad-Moghadam K, Youseftabar-Miri L (2011) Tetrahedron 67:5693

    Article  CAS  Google Scholar 

  53. Ziarani GM, Badiei A, Mousavi S, Lashgari N, Shahbazi A (2012) Chin J Catal 33:1832

    Article  Google Scholar 

  54. Safaei HR, Shekouhy M, Shirinfeshan A, Rahmanpur S (2012) Mol Divers 16:669

    Article  CAS  Google Scholar 

  55. Zou Y, Hu Y, Liu H, Shi D (2012) ACS Comb Sci 14:38

    Article  CAS  Google Scholar 

  56. Karmakar B, Nayak A, Banerji J (2012) Tetrahedron Lett 53:5004

    Article  CAS  Google Scholar 

  57. Guo RY, Wang P, Wang GD, Mo LP, Zhang ZH (2013) Tetrahedron 69:2056

    Article  CAS  Google Scholar 

  58. Ghahremanzadeh R, Rashid Z, Zarnani AH, Naeimi H (2013) Appl Catal A Gen 467:270

    Article  CAS  Google Scholar 

  59. Saluja P, Aggarwal K, Khurana JM (2013) Synth Commun 43:3239

    Article  CAS  Google Scholar 

  60. Thakur A, Tripathi M, Rajesh UC, Rawat DS (2013) RSC Adv 3:18142

    Article  CAS  Google Scholar 

  61. Satasia SP, Kalaria PN, Avalani JR, Raval DK (2014) Tetrahedron 70:5763

    Article  CAS  Google Scholar 

  62. Weitkamp J, Hunger M, Rymsa U (2001) Microporous Mesoporous Mater 48:255

    Article  CAS  Google Scholar 

  63. Niknam K, Sadeghi Habibabad M, Deris A, Aeinjamshid N (2013) Monatsh Chem 144:987

    Article  CAS  Google Scholar 

  64. Makvandi M, Abiar Dil F, Malekzadeh A, Baghernejad M, Niknam K (2013) Iran J Catal 3:221

    Google Scholar 

  65. Tayebi S, Baghernejad M, Saberi D, Niknam K (2011) Chin J Catal 32:1477

    Article  CAS  Google Scholar 

  66. Niknam K, Deris A, Naeimi F, Majleci F (2011) Tetrahedron Lett 52:4642

    Article  CAS  Google Scholar 

  67. Nouri Sefat M, Deris A, Niknam K (2011) Chin J Chem 29:2361

  68. Baghernejad M, Niknam K (2012) Int J Chem 4:52

    Article  CAS  Google Scholar 

  69. Niknam K, Jamali A, Tajaddod M, Deris A (2012) Chin J Catal 33:1312

    Article  CAS  Google Scholar 

  70. Pargaleh Brojeni S, Baghernejad M, Saberi D, Niknam K (2013) Green Chem Lett Rev 6:69

    Article  Google Scholar 

  71. Niknam K, Jamali A (2012) Chin J Catal 33:1840

    Article  CAS  Google Scholar 

  72. Niknam K, Borazjani N, Rashidian R, Jamali A (2013) Chin J Catal 34:2245

    Article  CAS  Google Scholar 

  73. Niknam K, Rashidian R, Jamali A (2013) Scientia Iran C 20:1863

    Google Scholar 

Download references

Acknowledgments

We are thankful to the Persian Gulf University Research Council for the partial support of this work. Also, we are thankful to the School of Chemistry, Manchester University for running NMRs.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran

    Khodabakhsh Niknam & Parisa Abolpour

Authors
  1. Khodabakhsh Niknam
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Parisa Abolpour
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Khodabakhsh Niknam.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 3608 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Niknam, K., Abolpour, P. Synthesis of spirooxindole pyrimidines catalyzed by silica-bonded N-propyltriethylenetetramine as a recyclable solid base catalyst in aqueous medium. Monatsh Chem 146, 683–690 (2015). https://doi.org/10.1007/s00706-014-1343-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1343-1

Keywords

Search

Navigation