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A Rhodamine-B Catalyzed Visible-Light-Mediated Benign Synthetic Route for 4,5-Dihydro-1H-pyrazoles

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Abstract

Herein, an apposite and straightforward methodology has been established for the synthesis of 4,5-dihydro-1H-pyrazole and its derivatives by using Chalcones and Hydrazines as substrates in EtOH under 20W CFL irradiation at room temperature. The distinctive trait of this protocol is the utilization of an efficient, green, highly water soluble organophotoredox catalyst “Rhodamine B”, a simple red xanthene dye, to create C–N bonds via formation of free radicals and eventually terminating with intramolecular cyclization. Short reaction time, environmentally benign approach, cost effectiveness, feasibility and adaptability with respect to a wide range of substrates and good to excellent yield of the product supplements the synthesis.

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References

  1. Kulshreshtha A (2015) Soc Issues Environ Probl 3:1

    Google Scholar 

  2. Ivankovic A, Dronjic A, Bevanda AM, Talic S (2017) IJSGE 6:39

    Article  CAS  Google Scholar 

  3. Lang X, Zhaob J, Xiaodong C (2016) Chem Soc Rev 45:3026–30386

    Article  CAS  PubMed  Google Scholar 

  4. Xu G, Xu P (2021) Chem Commun 57:12914–12935

    Article  CAS  Google Scholar 

  5. Chen J, Hu X, Lu L, Xiao W (2016) Chem Soc Rev 45:2044–2056

    Article  CAS  PubMed  Google Scholar 

  6. Dai C, Liu B (2020) Energy Environ Sci 13:24–52

    Article  CAS  Google Scholar 

  7. Uygur M, Danelzik T, Mancheño OG (2019) Chem Commun 55:2980–2983

    Article  CAS  Google Scholar 

  8. Srivastava V, Singh PP (2017) RSC Adv 7:31377–31392

    Article  ADS  CAS  Google Scholar 

  9. Peng Y, Feng CT, Li YQ, Chen FX, Xu K (2019) Org Biomol Chem 17:6570–6573

    Article  CAS  PubMed  Google Scholar 

  10. Saravanan R, Gupta VK, Narayanan V, Stephen A (2014) J Taiwan Inst Chem Eng 45:1910–1917

    Article  CAS  Google Scholar 

  11. Helm MPV, Klemm B, Eelkema R (2019) Nat Rev Chem 3:491–508

    Article  Google Scholar 

  12. Zhang JJ, Cheng YB, Duan XH (2017) Chin J Chem 35:311–315

    Article  CAS  Google Scholar 

  13. Xie LY, Hu JL, Song YX, Jia GK, Lin YW, He JY, Cao Z, He WM (2019) ACS Sustain Chem Eng 7:19993–19999

    Article  CAS  Google Scholar 

  14. Xie LY, Chen YL, Qin L, Wen Y, Xie JW, Tan JX, Huang Y, Cao Z, He WM (2019) Org Chem Front 6:3950–3955

    Article  CAS  Google Scholar 

  15. He H, Xu N, Zhang H, Chen B, Hu Z, Guo K, Chun J, Cao S, Zhu Y (2021) RSC Adv 11:17340–17345

    Article  ADS  CAS  PubMed  PubMed Central  Google Scholar 

  16. Aboul-Enein MN, El-Azzouny AA, Attia MI, Maklad YA, Amin KM, Abdel-Rehim M, El Behairy MF (2012) J Med Chem 47:360–369

    Article  CAS  Google Scholar 

  17. Li QS, Lv XH, Zhang YB, Dong JJ, Zhou WP, Yang Y, Zhu HL (2012) Bioorg Med Chem Lett 22:6596–6601

    Article  CAS  PubMed  Google Scholar 

  18. Goodell JR, Puig-Basagoiti F, Forshey BM, Shi PY, Ferguson DM (2006) J Med Chem 49:2127–2137

    Article  CAS  PubMed  Google Scholar 

  19. Agrawal M, Sonar PK, Saraf SK (2011) Med Chem Res 21:3376–3381

    Article  Google Scholar 

  20. Sivakumar PM, Seenivasan SP, Kumar V, Doble M (2010) Chem Lett 20:3169–3172

    Article  CAS  Google Scholar 

  21. Bhat P, Shridhar G, Ladage S, Ravishankar L (2017) J Chem Sci 129:1441–1448

    Article  CAS  Google Scholar 

  22. Gadekar SP, Pawar GT, Magar RR, Lande MK (2020) Polycycl Aromat Compd 40:126–134

    Article  CAS  Google Scholar 

  23. Pise AS, Jadhav SD, Burungale AS, Devkate SS, Gawade RB (2018) Asian J Chem 30:894–896

    Article  CAS  Google Scholar 

  24. Babiola AS, Pothiappan V, Subburethinam R (2018) RSC Adv 8:30071–30075

    Article  Google Scholar 

  25. Jaiswal D, Tiwari J, Singh S, Sharma AK, Singh J, Singh J (2018) Curr Organocatalysis 5:229–238

    Article  CAS  Google Scholar 

  26. Mishra A, Srivastava M, Rai P, Yadav S, Tripathi BP, Singh J, Singh J (2016) RSC Adv 6:49164–49172

    Article  ADS  CAS  Google Scholar 

  27. Mishra A, Jaiswal A, Sharma AK, Pandey YK, Singh J, Singh J (2023). Catal Lett. https://doi.org/10.1007/s10562-023-04279-1

    Article  Google Scholar 

  28. Mishra A, Rai P, Singh J, Singh J (2018) ChemistrySelect 3:8408–8414

    Article  CAS  Google Scholar 

  29. Mishra A, Rai P, Srivastava M, Tripathi BP, Yadav S, Singh J, Singh J (2017) Catal Lett 147:2600–2611

    Article  CAS  Google Scholar 

  30. Tripathi BP, Mishra A, Rai P, Pandey YK, Srivastava M, Yadav S, Singh J, Singh J (2017) New J Chem 41:11148–11154

    Article  Google Scholar 

  31. Sharma AK, Jaiswal A, Mishra A, Jaiswal D, Singh S, Singh J, Singh J (2020) New J Chem 44:13350–13356

    Article  CAS  Google Scholar 

  32. Yadav AK, Yadav LDS (2015) Org Biomol Chem 13:2606–2611

    Article  CAS  PubMed  Google Scholar 

  33. Bu MJ, Lu GP, Cai C (2016) Catal Sci Technol 6:413–416

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are thankful to SAIF, Punjab University, Chandigarh, India and SAIF, CDRI, Lucknow, India for providing spectral data. Prof. Jagdamba Singh acknowledges the financial support from UGC, New Delhi in the form of BSR Faculty Fellowship (No. F.18-1/2011 (BSR)).

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Authors and Affiliations

  1. Department of Chemistry, MKR Government Degree College, Saddique Nagar, Nandgram, Ghaziabad, Uttar Pradesh, India

    Anu Mishra

  2. Environmentally Benign Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad, 211002, India

    Yogesh Kumar Pandey & Jagdamba Singh

  3. Department of Chemistry, K.N. Government PG College, Gyanpur, Bhadohi, Uttar Pradesh, India

    Amit Kumar Sharma

  4. Department of Chemistry, Feroze Gandhi College, Raebareli, Uttar Pradesh, India

    Anjali Jaiswal

  5. Department of Chemistry, Government Degree College, Haripur, Nihastha, Raebareli, Uttar Pradesh, India

    Bhartendu Pati Tripathi

  6. Department of Chemistry, LRPG College, Uttar Pradesh, Sahibabad, India

    Jaya Singh

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  1. Anu Mishra
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  2. Yogesh Kumar Pandey
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  3. Amit Kumar Sharma
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  6. Jaya Singh
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  7. Jagdamba Singh
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Correspondence to Jagdamba Singh.

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Mishra, A., Pandey, Y.K., Sharma, A.K. et al. A Rhodamine-B Catalyzed Visible-Light-Mediated Benign Synthetic Route for 4,5-Dihydro-1H-pyrazoles. Catal Lett (2024). https://doi.org/10.1007/s10562-024-04591-4

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