Skip to main content
Log in

Dendritic Amine on Mesoporous Silica: First Organo Base Catalyst for Paal Knorr Reaction under Solvent Free Condition, A green approach

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

We report for the first time a simple, highly efficient and ecofriendly approach for the preparation of pyrrole derivatives in the presence of dendritic amine grafted on mesoporous silica under solvent free condition. We have synthesized and characterized the three generations of dendritic amine grafted on mesoporous silica (G0–G2) through a stepwise growth technique. The maximum yield was observed with third generation (G2) and the catalyst was easily separated from the reaction mixture. Studies showed that dendritic effect of amino groups on the catalyst was the driving force of the reaction pathway, which has led to the formation of pyrrole derivatives. The green aspect of the present method are use of metal free catalyst, low catalyst loading, shorter reaction times, organic solvents are not needed, facile work-up, purification of the products by non-chromatographic methods, the excellent yield of the products, room temperature and the reusability of the catalyst.

Graphical Abstract

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. Bhagiyalakshmi M, Park SD, Cha WS, Jang HT (2010) Appl Surf Sci 256:6660

    Article  CAS  Google Scholar 

  2. King ASH, Twyman LJ (2002) J Chem Soc 1: 2209

    Google Scholar 

  3. Esfahani MN, Baltork IM, Khosropour AR, Moghadam M, Mirkhani V, Tangestaninejad S (2013) J Mol Catal A 379: 243–254

    Google Scholar 

  4. Aghapoor K, Nia LE, Mohsenzadeh F, Morad MM, Balavar Y, Darabi HR (2012) J Organomet Chem 25: 708

    Google Scholar 

  5. Ferre M, Pleixats R, Chi Man MW, Cattoen X (2016) Green Chem 18: 881

    Article  CAS  Google Scholar 

  6. Chermahini AN, Omran MK, Dabbagh HA, Mohammadnezhad G, Teimouri A (2015) New J Chem 39:4814

    Article  Google Scholar 

  7. Lang LM, Li BJ, Liu W, Jiang L, Xu Z, Yin G (2010) Chem Commun 46:448

    Article  CAS  Google Scholar 

  8. Algarra M, Jimenez MV, Rodriguez-Castellon E, Jimenez-Lopez A, Jimenez J (2005) Chemosphere 59:779

    Article  CAS  Google Scholar 

  9. Mazloum-Ardakani M, Sheikh-Mohseni MA, Abdollahi-Alibeik M, Benvidi A (2012) Analyst 137:1950

    Article  CAS  Google Scholar 

  10. Xie T, Shi L, Zhang J, Zhang D (2014) Chem Commun 507250

    Article  CAS  Google Scholar 

  11. Sinija P S, Sreekumar K (2015) RSC Adv 5: 101176.

    Article  Google Scholar 

  12. Bhardwaj V, Gumber D, Abbot V, Dhimana S, Sharmaa P 2015 RSC Adv 5:15233.

    Article  CAS  Google Scholar 

  13. Kamal A, Faazil S, Malik MS, Balakrishna M, Bajee S, Siddiqui MRH, Alarifi A (2016) Arabian J Chem 9:542.

    Article  CAS  Google Scholar 

  14. Nun P, Dupuy S, Gaillard S, Poater A, Cavallod L, Nolan SP (2011) Catal Sci Technol 1:58.

    Article  CAS  Google Scholar 

  15. Forberg D, Obenauf J, Friedrich M, Huhne S, Mader W, Motzc G, Kempe R (2014) Catal Sci Technol 4:4188.

    Article  CAS  Google Scholar 

  16. Palacios F, Aparico D, Santos JM, Vicario JM (2001) Tetrahedron 57:1961

    Article  CAS  Google Scholar 

  17. Estevez V, Villacampa M, Menendez JC (2013) Chem Commun 49: 591

    Article  CAS  Google Scholar 

  18. Dieter RK, Yu H (2000) Org Lett 2: 2283

    Article  CAS  Google Scholar 

  19. Arcadi A, Rossi E (1998) Tetrahedron 54: 15253

    Article  CAS  Google Scholar 

  20. Lee CF, Yang LM, Hwu TY, Feng AS, Tseng JC, Luh TY (2000) J Am Chem Soc 122:4992

    Article  CAS  Google Scholar 

  21. Katritzky A, Jiang J, Steel PJ (1994) J Org Chem 59:4551

    Article  CAS  Google Scholar 

  22. Paul S, Das AR (2012) Catal Sci Technol 2: 1130

    Article  CAS  Google Scholar 

  23. Dong Y, Naranjan N, Ablaza SL, Yu SX, Bolvig S, Forsyth DA, Le Quesne PW (1999) J Org Chem 64: 2657

    Article  CAS  Google Scholar 

  24. Haubmann C, Huebner H, Gmeiner P (1999) Bioorg. Med. Chem. Lett. 9: 3143

    Article  CAS  Google Scholar 

  25. Robertson J, Hatley RJD, Watkin DJ (2000) J Chem Soc 1: 3389

    Google Scholar 

  26. Wurtz NR, Turner JM, Baird EE, Dervan PB (2001) Org Lett 3: 1201

    Article  CAS  Google Scholar 

  27. Chen J, Liu M, Yang X, Ding J, Wu H (2008) J Braz Chem Soc 19: 877

    Article  CAS  Google Scholar 

  28. Dou G, Shi C, Shi D (2008) J Comb Chem 10: 810

    Article  CAS  Google Scholar 

  29. Bharadwaj AR, Scheidt KA (2004) Org Lett 6: 2465

    Article  CAS  Google Scholar 

  30. Minetto G, Raveglia LF, Taddei M (2004) Org Lett 6: 3

    Article  Google Scholar 

  31. Akelis L, Rousseau J, Juskenas R, Dodonova J, Rousseau C, Menuel S, Prevost D, Tumkevicius S, Monflier E, Hapio F (2016) Eur J Org Chem. 1: 31

    Article  Google Scholar 

  32. Duan F, Ding J, Deng H, Chen D, Liu JCM, Wu H (2013) Chin Chem Lett 24: 793

    Article  CAS  Google Scholar 

  33. Neelakandeswari N, Sangami G, Emayavaramban P, Karvembu R, Dharmaraj N, Kim HY(2012) Tetrahedron Lett 53:2980

    Article  CAS  Google Scholar 

  34. Jalal S, Sarkar S, Bera K, Maiti S, Jana U (2013) Eur J Org Chem 4823.

  35. Phan NTS, Nguyen TT, Luu QH, Nguyen LTL 2012 J. Mol. Catal. A: Chem. 363: pp 178

  36. Darabi HR, Poorheravi MR, Aghapoor K, Mirzaee A, Mohsenzadeh F, Asadollahnejad N, Taherzadeh H, Balavar Y 2012 Environ. Chem. Lett. 10: pp 5

  37. Duan FJ, Ding JC, Deng HJ, Chen DB, Chen JX, Liu MC, Wu HY 2014 Chin Chem Lett 24793

  38. Su P, Chiu S, Lin Y 2016 Sens. Actuators, B224: 833.

  39. Rahmatpour A (2012) J Organomet Chem 712:15

    Article  CAS  Google Scholar 

  40. Polshettiwar V, Baruwati B, Varma RS 2009 Chem. Commun.1837

  41. Kim BH, Bae S, Go A, Lee H, Gong C, Lee BM 2016 Org Biomol Chem 14: 265

  42. Cho H, Madden R, Nisanci B, Torok B 2015 Green Chem 17: 1088

  43. Bora U, Saikia A, Boruah RC (2003) Org Lett 5: 435.

    Article  CAS  Google Scholar 

  44. Cho H, Torok F, Torok B (2014) Green Chem 16: 3623.

    Article  CAS  Google Scholar 

  45. Abid M, Spaeth A, Tcrck (2006) Adv Synth Catal 348:2191

    Article  CAS  Google Scholar 

  46. Abid M, Landge SM, Toriik (2006) Org Prep Proced Int 35: 495.

    Article  Google Scholar 

  47. Banik M, Ramirez B, Reddy A, Bandyopadhyay D, Banikl BK (2012) Org Med Chem Lett 2:11.

    Article  Google Scholar 

  48. Eftekhari-Sis B, Akbari A, Amirabed M (2011) Chem Heterocycl Compd 46: 11.

    Article  Google Scholar 

  49. Lapina I M, Pevzner LM, Potekhin AA,(2007) Russ J Gen Chem 77: 5.

    Article  Google Scholar 

  50. Makowska-Janusik M, Kassiba A, Errien N, Mehdi A 2010 J Inorg Organomet Polym. 20: pp 761

  51. Darabi HR, Aghapoor K, Farahani AD, Mohsenzadeh F 2012 Environ Chem Lett 10: 369

  52. Gao L, Bing L, Zhang Z, Kecheng H, Xiaoyun H, Deng K 2013 J. Organomet. Chem. 735: 26

  53. Jafari AA, Mahmoudi H 2013 Environ Chem Lett 11: 157

  54. Handy S, Lavender K (2013) Tetrahedron Lett 54: 4377.

    Article  CAS  Google Scholar 

  55. Cheraghi S, Saberi D, Heydari A 2014 Catal Lett 144: 1339

  56. Zhang X, Weng G, Zhang Y, Li Y 2015 Tetrahedron 71: 2595

  57. Samadi M, Behbahani FK (2015) J. Chil. Chem Soc 60.

  58. Sherly PB, Sreekumar K unpublished results

  59. Abbat S, Dhaked D, Arfeen M, Bharatam PV 2015 RSC Adv 5: 88353.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We would like to thank STIC, CUSAT, Dept. of Physics, CUSAT and IIT Delhi for assistance with various analyses. One of the authors (K. A. J) thanks the CSIR, Govt. of India for financial assistance in the form of fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. Sreekumar.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 800 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jisha, K.A., Sreekumar, K. Dendritic Amine on Mesoporous Silica: First Organo Base Catalyst for Paal Knorr Reaction under Solvent Free Condition, A green approach. Catal Lett 147, 964–975 (2017). https://doi.org/10.1007/s10562-017-1975-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-017-1975-y

Keywords

Navigation