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Fe3O4@Boehmite-NH2-CoII NPs: An Environment Friendly Nanocatalyst for Solvent Free Synthesis of Coumarin Derivatives Through Pechmann Condensation Reaction

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Abstract

We report herein the synthesis of coumarin derivatives via the Pechmann condensation reaction in the presence of magnetic core–shell-like Fe3O4@Boehmite-NH2-CoII NPs. The aforesaid nanocatalyst which previously reported by our group, was found to be an efficient heterogeneous nanocatalyst in this reaction. Initially, the reaction conditions were optimized with different solvents, catalyst amounts and temperatures. Subsequently, the scope of the reaction was extended and the coumarin derivatives were obtained in reasonable yields. Interestingly, Fe3O4@Boehmite-NH2-CoII NPs was stable under reaction conditions and can be reused at least six times without a significant decrease in its catalytic activity. More importantly, using cobalt as a non-toxic, inexpensive, widely available and high-activity catalyst is great of interest than the most previously reported protocols.

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References

  1. O’Kennedy R, Zhorenes RD (1997) Coumarins: biology, applications and mode of action. Wiley, Chichester

    Google Scholar 

  2. Kayser O, Kolodziej H (1997) Planta Med 63:508–510

    Article  CAS  PubMed  Google Scholar 

  3. Wang CJ, Hsieh YJ, Chu CY, Lim YL, Tseng TH (2002) Cancer Lett 183:163–168

    Article  CAS  PubMed  Google Scholar 

  4. Cravotto G, Nano GM, Palmisano G, Tagliapietra S (2001) Tetrahedron Asymm 12:707–709

    Article  CAS  Google Scholar 

  5. Fan GJ, Mar W, Park MK, Choi EW, Kim K, Kim S (2001) Bioorg Med Chem Lett 11:2361–2363

    Article  CAS  PubMed  Google Scholar 

  6. Kirkiacharian S, Thuy DT, Sicsic S, Bakhchianian R, Kurkjian R, Tonnaire T (2002) II Farmaco 57:703–708

    Article  CAS  Google Scholar 

  7. Maeda M (1984) Laser dyes. Academic, New York

    Google Scholar 

  8. Sethna SM, Shah NM (1945) Chem Rev 36:1–62

    Article  CAS  Google Scholar 

  9. Campos-Toimil M, Orallo F, Santana L, Uriarte E (2002) Bioorg Med Chem Lett 12:783–786

    Article  CAS  PubMed  Google Scholar 

  10. Elderfield RC, Mehta AC (1967) J Med Chem 10:921–923

    Article  CAS  PubMed  Google Scholar 

  11. Hong WP, Lee KJ (2005) Synthesis 1:33–38

    Google Scholar 

  12. Shaabani A, Ghadari R, Rahmati A, Rezayan AH (2009) J Iran Chem Soc 6:710–714

    Article  CAS  Google Scholar 

  13. Jones G (1967) Org React 15:204–599

    CAS  Google Scholar 

  14. Brufola G, Fringuelli F, Piermatti O, Pizzo F (1996) Heterocycles 43:1257–1266

    Article  CAS  Google Scholar 

  15. Johnson JR (1942) Org React 1:210–265

    Google Scholar 

  16. Shriner RL (1942) Org React 1:1–37

    Google Scholar 

  17. Yavari I, Hekmat-Shoar R, Zonouzi A (1998) Tetrahedron Lett 39:2391–2392

    Article  CAS  Google Scholar 

  18. Pechmann VH, Duisberg C (1884) Chem Ber 17:929–936

    Article  Google Scholar 

  19. Horning EC (1955) Organic synthesis. Wiley, New York

    Google Scholar 

  20. Karimi-Jaberi Z, Zarei L (2013) Acta Chim Slov 60:178–183

    CAS  PubMed  Google Scholar 

  21. Kumar V, Tomar S, Patel R, Yousaf A, Parmr VS, Malhotra SV (2008) Synth Commun 38:2646–2654

    Article  CAS  Google Scholar 

  22. Valizadeh H, Shockravi A (2005) Tetrahedron Lett 46:3501–3503

    Article  CAS  Google Scholar 

  23. Sethna SM, Shah NM, Shah RC (1938) J Chem Soc 228–232

  24. Karami B, Kiani M (2014) J Chin Chem Soc 61:213–216

    Article  CAS  Google Scholar 

  25. Gao ST, Li C, Wang Y, Ma JJ, Wang C, Zhang JW (2011) Synth Commun 41:1486–1491

    Article  CAS  Google Scholar 

  26. Dabiri M, Baghbanzadeh M, Kiani S, Vakilzadeh Y (2007) Monatsh Chem 138:997–999

    Article  CAS  Google Scholar 

  27. Smitha G, Sanjeeva Reddy Ch (2004) Synth Commun 34:3997–4003

    Article  CAS  Google Scholar 

  28. Bahekara SS, Shinde DB (2004) Tetrahedron Lett 45:7999–8001

    Article  CAS  Google Scholar 

  29. Rajabi F, Feiz A, Luque R (2015) Catal Lett 145:1621–1625

    Article  CAS  Google Scholar 

  30. Kabiri Esfahani F, Zareyee D, Yousefi R (2014) Chem Cat Chem 6:3333–3337

    Google Scholar 

  31. Rezaei R, Dorosty L, Rjabzade M, Khalifeh R (2011) Chin Chem Lett 22:1313–1316

    Article  CAS  Google Scholar 

  32. Abbasi Z, Rezayati S, Bagheri M, Hajinasiri R (2016) Chin Chem Lett 28:75–82

    Article  CAS  Google Scholar 

  33. Atghia SV, Sarvi Beigbaghlou S (2014) C R Chimie 17:1155–1159

    Article  CAS  Google Scholar 

  34. Nasseri MA, Sadeghzadeh SM (2014) J Iran Chem Soc 11:27–33

    Article  CAS  Google Scholar 

  35. Sun R, Gao Y, Ma Y, Yang G, Li Y (2017) J Iran Chem Soc 14:737–742

    Article  CAS  Google Scholar 

  36. Kangari S, Yavari I, Maasoumi B (2014) J Iran Chem Soc 12:1771–1779

    Article  CAS  Google Scholar 

  37. Karami B, Kiani M (2011) Catal Commun 14:62–67

    Article  CAS  Google Scholar 

  38. Kour M, Paul S (2017) Monatsh Chem 148:327–337

    Article  CAS  Google Scholar 

  39. Mobaraki A, Yasham S, Movassagh B (2015) Synlett 26:1263–1268

    Article  CAS  Google Scholar 

  40. Moradia L, Rabieib K, Belalia F (2016) Synth Commun 46:1283–1291

    Article  CAS  Google Scholar 

  41. Gunnewegh EA, Hoefnagel AJ, Bekkum HV (1995) J Mol Catal A Chem 100:87–92

    Article  CAS  Google Scholar 

  42. Sabou R, Hoelderich WF, Ramprasad D, Weinand R (2005) J Catal 232:34–37

    Article  CAS  Google Scholar 

  43. Palaniappan S, John A (2005) J Mol Catal A Chem 233:9–15

    Article  CAS  Google Scholar 

  44. Romanelli GP, Bennardi D, Ruiz DM, Baronetti G, Thomasb HJ, Autino JC (2004) Tetrahedron Lett 45:8935–8939

    Article  CAS  Google Scholar 

  45. Selvakumar S, Chidambaram M, Singh AP (2007) Catal Commun 8:777–783

    Article  CAS  Google Scholar 

  46. Mohammadinezhad A, Akhlaghinia B (2017) Green Chem 19:5625–5641

    Article  CAS  Google Scholar 

  47. Zarghani M, Akhlaghinia B (2015) Appl Organomet Chem 29:683–689

    Article  CAS  Google Scholar 

  48. Jahanshahi R, Akhlaghinia B (2016) RSC Adv 6:29210–29219

    Article  CAS  Google Scholar 

  49. Zarghani M, Akhlaghinia B (2016) RSC Adv 6:31850–31860

    Article  CAS  Google Scholar 

  50. Zarei Z, Akhlaghinia B (2016) RSC Adv 6:106473–106484

    Article  CAS  Google Scholar 

  51. Zarghani M, Akhlaghinia B (2016) RSC Adv 6:38592–38601

    Article  CAS  Google Scholar 

  52. Ghasemzadeh MS, Akhlaghinia B (2017) Bull Chem Soc Jpn 90:1119–1128

    Article  CAS  Google Scholar 

  53. Jahanshahi R, Akhlaghinia B (2017) Catal Lett 147:2640–2655

    Article  CAS  Google Scholar 

  54. Nejatianfar M, Akhlaghinia B, Jahanshahi R (2018) Appl Organomet Chem 32:4095–4107

    Article  CAS  Google Scholar 

  55. Zarei Z, Akhlaghinia B (2017) New J Chem 41:15485–15500

    Article  CAS  Google Scholar 

  56. Zarei Z, Akhlaghinia B (2018) Turk J Chem 42:170–191

    Article  CAS  Google Scholar 

  57. Ghasemzadeh MS, Akhlaghinia B (2018) ChemistrySelect 3:3161–3170

    Article  CAS  Google Scholar 

  58. Zamani M, Akhlaghinia B, Mohammadinezhad A (2018) ChemistrySelect 3:9431–9442

    Article  CAS  Google Scholar 

  59. Prateeptongkum S, Duangdee N, Thongyoo P (2015) Arkivoc 2015:248–258

    Article  CAS  Google Scholar 

  60. Jung K, Park YJ, Ryu JS (2008) Synth Commun 38:4395–4406

    Article  CAS  Google Scholar 

  61. Rodríguez-Domínguez JC, Kirsch G (2006) Synthesis 11:1895–1897

    Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the partial support of this study by Ferdowsi University of Mashhad Research Council (Grant No. p/3/47339).

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Correspondence to Batool Akhlaghinia.

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Pakdel, S., Akhlaghinia, B. & Mohammadinezhad, A. Fe3O4@Boehmite-NH2-CoII NPs: An Environment Friendly Nanocatalyst for Solvent Free Synthesis of Coumarin Derivatives Through Pechmann Condensation Reaction. Chemistry Africa 2, 367–376 (2019). https://doi.org/10.1007/s42250-019-00042-5

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  • DOI: https://doi.org/10.1007/s42250-019-00042-5

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