Skip to main content
Log in

Amidosulfonic acid supported on graphitic carbon nitride: novel and straightforward catalyst for Paal–Knorr pyrrole reaction under mild conditions

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

Abstract

A novel heterogeneous acidic catalyst was prepared by in situ immobilization of amidosulfonic acid (NH2SO3H) on graphitic carbon nitride (g-C3N4) under hydrothermal conditions. The textural morphology of NH2SO3H/g-C3N4 nanocomposite was characterized via powder X-ray diffraction, FT-IR, TGA, EDX, and scanning electron microscopy. The spatial arrangement of the amidosulfonic acid on the surface of g-C3N4 leads to the construction of a unique solid acid structure, resulting in a substantial enhancement of catalytic activity toward a high efficient preparation of pyrroles by Paal–Knorr reaction. The reactions undergo completion readily with good to excellent yields, with simple purification in an environmentally friendly manner. The NH2SO3H/g-C3N4 nanocomposite can be readily recycled, and no noteworthy reduction in the catalytic activity detected after four runs.

Graphic 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.

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

Similar content being viewed by others

References

  1. Gu Y, Jérôme F (2013) Chem Soc Rev 42:9550

    Article  CAS  PubMed  Google Scholar 

  2. Gu Y, Jerome F (2010) Green Chem 12:1127

    Article  CAS  Google Scholar 

  3. Chakraborti AK, Rudrawar S, Jadhav KB, Kaur G, Chankeshwara SV (2007) Green Chem 9:1335

    Article  CAS  Google Scholar 

  4. Chakraborti AK, Roy SR, Kumar D, Chopra P (2008) Green Chem 10:1111

    Article  CAS  Google Scholar 

  5. Liu P, Hao JW, Mo LP, Zhang ZH (2015) RSC Adv 5:48675

    Article  CAS  Google Scholar 

  6. Ma CT, Liu P, Wu W, Zhang ZH (2017) J Mol Liq 242:606

    Article  CAS  Google Scholar 

  7. Brahmachari G, Banerjee B (2014) ACS Sustainable Chem Eng 2:411

    Article  CAS  Google Scholar 

  8. Brahmachari G, Banerjee B (2014) ACS Sustain Chem Eng 2:2802

    Article  CAS  Google Scholar 

  9. Du YR, Xu BH, Pan JS, Wu YW, Peng XM, Wang YF, Zhang SJ (2019) Green Chem 21:4792

    Article  CAS  Google Scholar 

  10. Deng J, Xu BH, Wang YF, Mo XE, Zhang R, Li Y, Zhang SJ (2017) Catal Sci Technol 7:2065

    Article  CAS  Google Scholar 

  11. Xu BH, Wang JQ, Sun J, Huang Y, Zhang JP, Zhang XP, Zhang SJ (2015) Green Chem 17:108

    Article  CAS  Google Scholar 

  12. Liang Q, Liu X, Wang J, Liu Y, Liu Z, Tang L, Shao B, Zhang W, Gong SH, Cheng M, He Q, Feng CH (2021) J Hazard Mater 401:123355

    Article  CAS  PubMed  Google Scholar 

  13. Dong G, Zhang Y, Pan Q, Qiu J (2014) J Photochem Photobiol 20:33

    Article  CAS  Google Scholar 

  14. Soleymani Ahooie T, Azizi N, Yavari I, Mahmoudi Hashemi M (2018) J Iran Chem Soc 15:855

    Article  Google Scholar 

  15. Zhang L, Zhang J, Ma J, Cheng DJ, Tan B (2017) J Am Chem Soc 139:1714

    Article  CAS  PubMed  Google Scholar 

  16. Miller TS, Jorge AB, Suter TM, Sella A, Cora F, McMillan PF (2017) PhysChemPhys 19:15613

    CAS  Google Scholar 

  17. Savateev A, Ghosh I, König B, Antonietti M (2018) Angew Chem Int Ed 57:15936

    Article  CAS  Google Scholar 

  18. Di JQ, Zhang M, Chen YX, Wang JX, Geng SS, Tang JQ, Zhang ZH (2021) Green Chem 23:1041

    Article  CAS  Google Scholar 

  19. Zhang M, Sun W, Lv H, Zhang ZH (2021) Curr Opin Green Sustain Chem 27:100390

    Article  Google Scholar 

  20. Gong Y, Li M, Li H, Wang Y (2015) Green Chem 17:715

    Article  CAS  Google Scholar 

  21. Gao G, Di JQ, Zhang HY, Mo LP, Zhang ZH (2020) J Catal 387:39

    Article  CAS  Google Scholar 

  22. Cao Q, Kumru B, Antonietti M, Schmidt BVKJ (2020) Mater Horiz 7:762

    Article  CAS  Google Scholar 

  23. Navalon S, Dhakshinamoorthy A, Alvaro M, Antonietti M, García H (2017) Chem Soc Rev 46:4501

    Article  CAS  PubMed  Google Scholar 

  24. Wang J, Wang G, Cheng B, Yu J, Fan J (2021) Chin J Catal 42:56

    Article  CAS  Google Scholar 

  25. Goyal S, Patel K, Gangar M, Kumar K, Nair V (2015) RSC Adv 5:3187

    Article  CAS  Google Scholar 

  26. Patil RN, Kumar AV (2018) ChemistrySelect 3:9812

    Article  CAS  Google Scholar 

  27. Gong Z, Lei Y, Zhou P, Zhang Z (2017) New J Chem 41:10613

    Article  CAS  Google Scholar 

  28. Chen W, Wang J (2013) Organometallics 32:1958

    Article  CAS  Google Scholar 

  29. Nguyen HT, Nguyen LHT, Doan TLH, Tran PH (2019) RSC Adv 9:9093

    Article  CAS  Google Scholar 

  30. Hu HC, Liu YH, Li BL, Cui ZS, Zhang ZH (2015) RSC Adv 5:7720

    Article  CAS  Google Scholar 

  31. Li BL, Hu HC, Mo LP, Zhang ZH (2014) RSC Adv 4:12929

    Article  CAS  Google Scholar 

  32. Cho H, Madden R, Nisanci B, Török B (2015) Green Chem 17:1088

    Article  CAS  Google Scholar 

  33. Zhang ZH, Li JJ, Li TS (2008) Ultrason Sonochem 15:673

    Article  CAS  PubMed  Google Scholar 

  34. Rajeshkumar V, Neelamegam C, Anandan S (2019) Synthesis 51:4023

    Article  CAS  Google Scholar 

  35. Shaibuna M, Theresa LV, Sreekumar K (2018) Catal Lett 148:2359

    Article  CAS  Google Scholar 

  36. Edrisi M, Azizi N (2020) J Iran Chem Soc 17:901

    Article  CAS  Google Scholar 

  37. Saidi MR, Azizi N, Zali-Boinee H (2001) Tetrahedron 57:6829

    Article  CAS  Google Scholar 

  38. Azizi N, Mariami M, Edrisi M (2014) Dyes Pigm 100:215

    Article  CAS  Google Scholar 

  39. Azizi N, Baghi R, Ghafuri H, Bolourtchian M, Hashemi M (2010) Synlett 2010:379–382

    Article  Google Scholar 

  40. De SK (2008) Catal Lett 124:174

    Article  CAS  Google Scholar 

  41. Wani RR, Chaudhari Hemchandra K, Takale BS (2019) J Heterocycl Chem 56:1337

    Article  CAS  Google Scholar 

  42. Rahmatpour A, Aalaie J (2011) J Heteroat Chem 22:85

    Article  CAS  Google Scholar 

  43. He YH, Wang GQ, Guan Z (2010) J Heterocycl Chem 47:487

    Google Scholar 

  44. Hyejin C, Fanni T, Bela T (2014) Green Chem 16:3623

    Article  Google Scholar 

  45. Schmidt EY, Semenova NV, Ivanova EV, Bidusenko IA, Trofimov BA (2020) Mendeleev Commun 30:109

    Article  CAS  Google Scholar 

  46. Azizi N, Davoudpour A, Eskandari F, Bateb E (2013) Monatsh Chem 144:405

    Article  CAS  Google Scholar 

  47. Peglow TJ, Gabriel DCP, Duarte LFB, Silva MS, Barcellos T, Perin G, Alves D (2019) J Org Chem 84:5471

    Article  CAS  PubMed  Google Scholar 

  48. Azizi N, Khajeh-Amiri A, Ghafuri H, Bolourtchian M, Saidi MR (2009) Synlett 14:2245

    Article  Google Scholar 

  49. Ma FP, Li PH, Li BL, Mo LP, Liu N, Kang HJ, Liu YN, Zhang ZH (2013) Applied Catal A 457:34

    Article  CAS  Google Scholar 

  50. Zuo B, Chen J, Liu M, Ding J, Wu H, Su W (2009) J Chem Res 1:14

    Article  Google Scholar 

  51. Lee CK, Jun JH, Yu JS (2000) J Heterocycl Chem 37:15

    Article  CAS  Google Scholar 

  52. Lee H, Kim BH (2013) Tetrahedron 69:6698

    Article  CAS  Google Scholar 

  53. Chen X, Yang M, Zhou M (2016) Tetrahedron Lett 57:5215

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support of this work by Chemistry and Chemical Engineering Research Center of Iran is gratefully appreciated.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Najmedin Azizi.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Azhdari, A., Azizi, N., Sanaeishoar, H. et al. Amidosulfonic acid supported on graphitic carbon nitride: novel and straightforward catalyst for Paal–Knorr pyrrole reaction under mild conditions . Monatsh Chem 152, 625–634 (2021). https://doi.org/10.1007/s00706-021-02771-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02771-1

Keywords

Navigation