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β-CD-SO3H: Synthesis, Characterization and Its Application for the Synthesis of Benzylpyrazolyl Naphthoquinone and Pyrazolo Pyranopyrimidine Derivatives in Water

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Abstract

Green and economical method has been reported for the synthesis of benzylpyrazolyl naphthoquinone and pyrazolo pyranopyrimidines in water at room temperature by using β-CD-SO3H. β-Cyclodextrin supported sulfonic acid was prepared by simple one step procedure and characterized by FT-IR spectrum, 1H NMR, 13C NMR spectra, TGA, EDAX, XRD, BET surface area analysis and acid–base titration. The present protocol is environmental benign due to heterogeneous reusable catalyst and green reaction medium. This methodology provides excellent yield of the desired product with short reaction time at room temperature, easy workup procedure and no need of column chromatographic separation. Pyrazolyl derivatives are of much importance because this fragment is a key moiety in numerous biologically active compounds.

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References

  1. Ruhul AM, Kalam MA, Masjuki HH, Fattah IMR, Reham SS, Rashed MM (2015) RSC Adv 5:101023–101044

    CAS  Google Scholar 

  2. Zhou Y, Chen G, Long Z, Wang J (2014) RSC Adv 4:42092–42113

    CAS  Google Scholar 

  3. Nidheesh PV (2015) RSC Adv 5:40552–40577

    CAS  Google Scholar 

  4. Liu J, Chen L, Cui H, Zhang J, Zhang L, Su CY (2014) Chem Soc Rev 43:6011–6061

    CAS  PubMed  Google Scholar 

  5. Xue Z, Ma M-G, Li Z, Mu T (2016) RSC Adv 6:98874–98892

    CAS  Google Scholar 

  6. Santoro S, Kozhushkov SI, Ackermann L, Vaccaro L (2016) Green Chem 18:3471–3493

    CAS  Google Scholar 

  7. Khalafi-Nezhad A, Mohammadi S (2013) RSC Adv 3:4362–4371

    CAS  Google Scholar 

  8. Taheri M, Ghiaci M, Shchukarev A (2018) New J Chem 42:587–597

    CAS  Google Scholar 

  9. Sun J, Wang J, Cheng W, Zhang J, Li X, Zhang S, She Y (2012) Green Chem 14:654–660

    CAS  Google Scholar 

  10. Kaboudin B, Mostafalu R, Yokomatsu T (2013) Green Chem 15:2266–2274

    CAS  Google Scholar 

  11. Jean-Marie A, Griboval-Constant A, Khodakov AY, Monflier E, Diehl F (2011) Chem Commun 47:10767–10769

    CAS  Google Scholar 

  12. Salamatmanesh A, Miraki MK, Yazdani E, Heydari A (2018) Catal Lett 148:3257–3268

    CAS  Google Scholar 

  13. Wu J, Xu FZ, Feng SL, Xue W, Wang ZZ (2016) Heterocycles 92:1629–1642

    CAS  Google Scholar 

  14. Yadav GD, Kantam ML, Bhanage BM (2017) ACS Sustain Chem Eng 5:3597–3597

    CAS  Google Scholar 

  15. Urmode TD, Dawange MA, Shinde VS, Kusurkar RS (2017) Tetrahedron 73:4348–4354

    CAS  Google Scholar 

  16. Hapiot F, Monflier E (2017) Catalysts 7:173–184

    Google Scholar 

  17. Asghari S, Tajbakhsh M, Kenari BJ, Khaksar S (2011) Chin Chem Lett 22:127–130

    CAS  Google Scholar 

  18. Thombal RS, Jadhav AR, Jadhav VH (2015) RSC Adv 5:12981–12986

    CAS  Google Scholar 

  19. Wu J, Du X, Ma J, Zhang Y, Shi Q, Luo L, Song B, Yang S, Deyu H (2014) Green Chem 16:3210–3217

    CAS  Google Scholar 

  20. Girish YR, Sharath Kumar KS, Thimmaiah KN, Rangappa KS, Shashikanth S (2015) RSC Adv 5:75533–75546

    CAS  Google Scholar 

  21. Sabzi NE, Kiasat AR (2018) Catal Lett 148:2654–2664

    CAS  Google Scholar 

  22. Rai P, Srivastava M, Yadav S, Singh J, Singh J (2015) Catal Lett 145:2020–2028

    CAS  Google Scholar 

  23. Tayade YA, Patil DR, Wagh YB, Jangle AD, Dalal DS (2015) Tetthedron Lett 56:666–673

    CAS  Google Scholar 

  24. Patil DR, Ingole PG, Singh K, Dalal DS (2013) J Incl Phenom Macrocycl Chem 76:327–332

    CAS  Google Scholar 

  25. Tayade YA, Dalal DS (2017) Catal Lett 147:1411–1421

    Google Scholar 

  26. Sudhan PN, Ghashang M, Mansoor SS (2016) BJBAS 5:340–349

    Google Scholar 

  27. Gong K, Wang H, Ren X, Wang Y, Chen J (2015) Green Chem 17:3141–3147

    CAS  Google Scholar 

  28. Molnar A, Papp A (2014) Catal Sci Technol 4:295–310

    CAS  Google Scholar 

  29. Che F, Wang Y, Shen T, An X, Song Q (2015) C R Chimie 18:607–610

    CAS  Google Scholar 

  30. Gu Y (2012) Green Chem 14:2091–2128

    CAS  Google Scholar 

  31. Brahmachari G (2015) ACS Sustain Chem Eng 3:2058–2066

    CAS  Google Scholar 

  32. Shen T, Fu Z, Che F, Dang H, Lin Y, Song Q (2015) Tetrahedron Lett 56:1072–1075

    CAS  Google Scholar 

  33. Rigi F, Shaterian HR (2017) Polycycl Aromat Comp 37:314–326

    CAS  Google Scholar 

  34. Maleki A, Jafari AA, Yousefi S (2017) Carbohydr Polym 175:409–416

    CAS  PubMed  Google Scholar 

  35. Bakherad M, Doosti R, Mirzaee M, Jadidi K (2017) IJC 7:27–35

    CAS  Google Scholar 

  36. Khalafi-Nezhad A, Shahidzadeh ES, Sarikhani S, Panahi F (2013) Tetrahedron Lett 379:1–8

    CAS  Google Scholar 

  37. Panda S, Roy A, Deka SJ, Trivedi V, Manna D (2016) ACS Med Chem Lett 7:1167–1172

    CAS  PubMed  PubMed Central  Google Scholar 

  38. Fu Z, Qian K, Li S, Shen T, Song Q (2016) Tetrahedron Lett 57:1104–1108

    CAS  Google Scholar 

  39. Wang SL, Ding J, Shi F, Liu YP, Jiang B, Ma N, Tu SJ (2012) J Heterocycl Chem 49:521

    CAS  Google Scholar 

  40. Kumar M, Sribalan R, Padmini V (2017) ChemistrySelect 2:489–493

    CAS  Google Scholar 

  41. Lakshmanan S, Ramalakshmi N (2016) Synth Commun 46:2045–2052

    CAS  Google Scholar 

  42. Li XT, Zhao AD, Mo LP, Zhang ZH (2014) RSC Adv 4:51580–51588

    CAS  Google Scholar 

  43. Sadjadi S, Heravi MM, Daraie M (2017) Res Chem Intermed 43:2201–2214

    CAS  Google Scholar 

  44. Bakherad M, Keivanloo A, Gholizadeh M, Doosti R, Javanmardi M (2017) Res Chem Intermed 43:1013–1029

    CAS  Google Scholar 

  45. Nasresfahani Z, Kassaee MZ (2017) ChemistrySelect 2:9642–9646

    CAS  Google Scholar 

  46. Tipale MR, Khillare LD, Deshmukh AR, Bhosale MR (2018) J Heterocycl Chem 00:00

    Google Scholar 

  47. Ziarani GM, Aleali F, Lashgari N, Badiei A, Soorkic AA (2018) IJPR 17:525–534

    CAS  Google Scholar 

  48. Heravi MM, Mousavizadeh F, Ghobadi N, Tajbakhsh M (2014) Tetrahedron Lett 55:1226–1228

    CAS  Google Scholar 

  49. Dastkhoon S, Tavakoli Z, Khodabakhshi S, Baghernejad M, Abbasabadi MK (2015) New J Chem 39:7268–7271

    CAS  Google Scholar 

  50. Ganesan A, Kothandapani J, Subramaniapillai SG (2016) RSC Adv 6:20582–20587

    CAS  Google Scholar 

  51. Patil A, Salunkhe R (2018) Res Chem Intermed 44:3337–3348

    CAS  Google Scholar 

  52. Lohar T, Kumbhar A, Patil A, Kamat S, Salunkhe R (2019) Res Chem Intermed 45:1639–1651

    CAS  Google Scholar 

  53. Mane AH, Patil AD, Kamat SR, Salunkhe RS (2018) ChemistrySelect 3:6454–6458

    CAS  Google Scholar 

  54. Patil A, Mane A, Kamat S, Lohar T, Salunkhe R (2019) Res Chem Intermed 45:3441–3452

    CAS  Google Scholar 

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Acknowledgements

The authors would like to thank Department of Chemistry, Shivaji University, Kolhapur for providing research facility.

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Correspondence to Rajashri Salunkhe.

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Patil, A., Gajare, S., Rashinkar, G. et al. β-CD-SO3H: Synthesis, Characterization and Its Application for the Synthesis of Benzylpyrazolyl Naphthoquinone and Pyrazolo Pyranopyrimidine Derivatives in Water. Catal Lett 150, 127–137 (2020). https://doi.org/10.1007/s10562-019-02928-y

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