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Environmentally friendly synthesis of Ag/SiO2 nanoparticles using Thymus kotschyanus extract and its application as a green catalyst for synthesis of spirooxindoles

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Abstract

Today, plant extracts based on synthetic procedures have drawn consideration over conventional methods like physical and chemical procedures to synthesize nanomaterials. Green synthesis of nanomaterials has become an area of interest because of numerous advantages such as non-hazardous, economical, and feasible methods with a variety of applications in biomedicine, nanotechnology and nano-optoelectronics and as catalysts for various organic transformations. In this research, silver nanoparticles were deposited on the surface of nano-silica spheres by an in-situ reduction of Ag+ ions using an aqueous extract of Thymus kotschyanus aerial parts as a natural reducing and a capping agent. The result recorded from ultraviolet–visible (UV–Vis) spectrometer, Fourier transform infrared spectroscopy (FT-IR), thermal gravimetric analysis, scanning electron microscopy with energy-dispersive X-ray spectroscopy (SEM–EDS) and X-ray powder diffraction supports the biosynthesis and characterization of Ag/SiO2 nanoparticles. The results indicated that the average size of Ag/SiO2 nanoparticles is 25–60 nm. The Ag/SiO2 nanoparticles act as an environmentally friendly heterogeneous catalyst in the synthesis of spirooxindoles via the three-component condensation reaction of isatins, activated methylene reagents, and 1,3-dicarbonyl compounds in aqueous media, and the desired products were obtained with yields ranging from 90 to 98%. The catalyst can be recovered easily and used repetitively without significant loss of catalytic activity.

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References

  1. J.S. Wilkes, Green Chem. 4, 73 (2002)

    Article  CAS  Google Scholar 

  2. P. Anastas, N. Eghbali, Chem. Soc. Rev. 39, 301 (2010)

    Article  CAS  PubMed  Google Scholar 

  3. X.Y. Li, Y. Liu, X.L. Chen, X.Y. Lu, X.X. Liang, S.S. Zhu, C.W. Wei, L.B. Qu, B. Yu, Green Chem. 22, 4445 (2020)

    Article  CAS  Google Scholar 

  4. Z. Sadri, F.K. Behbahani, COS 17, 324 (2020)

    Article  CAS  Google Scholar 

  5. K.D. Dwivedi, B. Borah, L.R. Chowhan, Front. Chem. 7, 944 (2020)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  6. K. Verma, Y.K. Tailor, S. Khandelwal, M. Agarwal, E. Rushell, Y. Kumari, K. Awasthi, M. Kumar, RSC Adv. 8, 30430 (2018)

    Article  CAS  Google Scholar 

  7. L. Dai, K. Mao, Z. Pan, L. Rong, Res. Chem. Intermed. 45, 769 (2019)

    Article  CAS  Google Scholar 

  8. V.M. Muzalevskiy, K.V. Belyaeva, B.A. Trofimov, V.G. Nenajdenko, Green Chem. 21, 6353 (2019)

    Article  CAS  Google Scholar 

  9. J. Feng, S. Wang, J. Feng, Q. Li, J. Yue, G. Yue, P. Zou, G. Wang, New J. Chem. 44, 11937 (2020)

    Article  CAS  Google Scholar 

  10. Y.C. Wang, J.L. Wang, K.S. Burgess, J.W. Zhang, Q.M. Zheng, Y.D. Pu, L.J. Yan, X.B. Chen, RSC Adv. 8, 5702 (2018)

    Article  CAS  Google Scholar 

  11. C.J. Li, T.H. Chan, Organic reactions in aqueous media (Wiley, New York, 1997)

    Google Scholar 

  12. H.C. Hailes, Org. Process. Res. Dev. 11, 114 (2007)

    Article  CAS  Google Scholar 

  13. K. Zhang, J.M. Suh, J.W. Choi, H.W. Jang, M. Shokouhimehr, R.S. Varma, ACS Omega 4, 483 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. D. Raja, A. Philips, P. Palani, W.Y. Lin, S. Devikala, G.C. Senadi, J. Org. Chem. 8, 11531 (2020)

    Article  CAS  Google Scholar 

  15. T.N. Ansari, J.B. Jasinski, D.K. Leahy, S. Handa, J. Am. Chem. Soc. 1, 308 (2021)

    CAS  Google Scholar 

  16. O. Gherasim, R.A. Puiu, A.C. Bîrcă, A.C. Burdușel, A.M. Grumezescu, Nanomaterials 10, 2318 (2020)

    Article  CAS  PubMed Central  Google Scholar 

  17. K.V. Alex, P.T. Pavai, R. Rugmini, M.S. Prasad, K. Kamakshi, K.C. Sekhar, ACS Omega 5, 13123 (2020)

    Article  CAS  Google Scholar 

  18. P. Mathur, S. Jha, S. Ramteke, N.K. Jain, Artif. Cells. Nanomed Biotechnol. 46, 115 (2018)

    Article  CAS  PubMed  Google Scholar 

  19. M. Bhagat, R. Anand, R. Datt, V. Gupta, S. Arya, J. Inorg. Organomet. Polym. Mater. 29, 1039 (2019)

    Article  CAS  Google Scholar 

  20. L. Huang, Y. Sun, S. Mahmud, H. Liu, J. Inorg. Organomet. Polym. Mater. 30, 1653 (2020)

    Article  CAS  Google Scholar 

  21. W. Ali, V. Shabani, M. Linke, S. Sayin, B. Gebert, S. Altinpinar, M. Hildebrandt, J.S. Gutmann, T. Mayer-Gall, RSC Adv. 9, 4553 (2019)

    Article  CAS  Google Scholar 

  22. L. Zhu, H. Dai, S. Zhang, D. Hu, Q. Zhou, M. Zou, J. Adkins, J. Zheng, Anal. Lett. 52, 2868 (2019)

    Article  CAS  Google Scholar 

  23. X.Y. Dong, Z.W. Gao, K.F. Yang, W.Q. Zhang, L.W. Xu, Catal. Sci. Technol. 5, 2554 (2015)

    Article  CAS  Google Scholar 

  24. R.B. Nasir Baig, R.S. Varma, ACS Sustain. Chem. Eng. 1, 805 (2013)

    Article  CAS  Google Scholar 

  25. R. Baharfar, R. Azimi, Synth. Commun. 44, 89 (2014)

    Article  CAS  Google Scholar 

  26. M. Cobos, I. De-La-Pinta, G. Quindós, M.J. Fernández, M.D. Fernández, Nanomaterials 10, 376 (2020)

    Article  CAS  PubMed Central  Google Scholar 

  27. R. Poreddy, E.J. García-Suárez, A. Riisager, S. Kegnæs, Dalton. Trans. 43, 4255 (2014)

    Article  CAS  PubMed  Google Scholar 

  28. J.X. Zhao, R.N. Shi, Y.H. Quan, J.J. Liu, J. Wang, Y.L. Pei, X.H. Wang, Z. Li, J. Ren, Chem. Eng. Sci. 207, 1060 (2019)

    Article  CAS  Google Scholar 

  29. X. Pei, Y. Li, Y. Deng, L. Lu, W. Li, R. Shi, A. Lei, L. Zhang, Carbohydr. Polym. 251, 117020 (2021)

    Article  CAS  PubMed  Google Scholar 

  30. Z. Zhang, Y. Jiang, M. Chi, Z. Yang, C. Wang, X. Lu, RSC Adv. 5, 94456 (2015)

    Article  CAS  Google Scholar 

  31. V.G. Pol, D.N. Srivastava, O. Palchik, V. Palchik, M.A. Slifkin, A.M. Weiss, A. Gedanken, Langmuir 18, 3352 (2002)

    Article  CAS  Google Scholar 

  32. Z. Jiang, C. Liu, J. Phys. Chem. B 107, 12411 (2003)

    Article  CAS  Google Scholar 

  33. Y. Kobayashi, V. Salgueiriño-Maceira, L.M. Lizmarzán, Chem. Mater. 13, 1630 (2001)

    Article  CAS  Google Scholar 

  34. W. Chen, J. Zhang, Scr. Mater. 49, 321 (2003)

    Article  CAS  Google Scholar 

  35. H. Ramadoss, D. Saravanan, S.P. Sudhan, S.S. Mansoor, Der. Pharm. Lett. 8, 25 (2016)

    Google Scholar 

  36. K. Ding, Y. Lu, Z. Nikolovska-Coleska, S. Qiu, Y. Ding, W. Gao, J. Stuckey, K. Krajewski, P.P. Roller, Y. Tomita, D.A. Parrish, J.R. Deschamps, S. Wang, J. Am. Chem. Soc. 127, 10130 (2005)

    Article  CAS  PubMed  Google Scholar 

  37. S. Mathusalini, T. Arasakumar, K. Lakshmi, C.H. Lin, P.S. Mohan, M.G. Ramnath, R. Thirugnanasampandan, New J. Chem. 40, 5164 (2016)

    Article  CAS  Google Scholar 

  38. A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna, S.M. El-Bady, Bioorg. Med. Chem. 12, 2483 (2004)

    Article  CAS  PubMed  Google Scholar 

  39. G. Kumari, M. Modi, S.K. Gupta, R.K. Singh, Eur. J. Med. Chem. 46, 1181 (2011)

    Article  CAS  PubMed  Google Scholar 

  40. V.V. Vintonyak, K. Warburg, H. Kruse, S. Grimme, K. Hübel, D. Rauh, H. Waldmann, Angew. Chem. Int. Ed. Engl. 49, 5902 (2010)

    Article  CAS  PubMed  Google Scholar 

  41. S.T. Hilton, T.C.T. Ho, G. Pljevaljcic, K. Jones, Org. Lett. 2, 2639 (2000)

    Article  CAS  PubMed  Google Scholar 

  42. S.P. Baran, R.M. Richter, J. Am. Chem. Soc. 127, 15394 (2005)

    Article  CAS  PubMed  Google Scholar 

  43. M.Y. Chang, C.L. Pai, Y.H. Kung, Tetrahedron Lett. 46, 8463 (2005)

    Article  CAS  Google Scholar 

  44. J. Ma, S.M. Hecht, Chem. Commun. 1190 (2004)

  45. S. Edmondson, S.J. Danishefsky, L. Sepplorenzinol, N. Rosen, J. Am. Chem. Soc. 121, 2147 (1999)

    Article  CAS  Google Scholar 

  46. Y. Wang, A.A. Cobo, A.K. Franz, Org. Chem. Front. 8, 4315 (2021)

    Article  CAS  Google Scholar 

  47. G.J. Mei, F. Shi, Chem. Commun. 54, 6607 (2018)

    Article  CAS  Google Scholar 

  48. L.J. Yan, Y.C. Wang, Chem. Select. 1, 6948 (2016)

    CAS  Google Scholar 

  49. D. Cheng, Y. Ishihara, B. Tan, C.F. Barbas, ACS Catal. 4, 743 (2014)

    Article  CAS  Google Scholar 

  50. L. Hong, R. Wang, Adv. Synth. Catal. 355, 1023 (2013)

    Article  CAS  Google Scholar 

  51. X.N. Zhang, Y.X. Li, Z.H. Zhang, Tetrahedron 67, 7426 (2011)

    Article  CAS  Google Scholar 

  52. A. Kamal, K.S. Babu, M.V.P.S.V. Vardhan, S.M.A. Hussaini, R. Mahesh, S.P. Shaik, A. Alarifi, Bioorg. Med. Chem. Lett. 25, 2199 (2015)

    Article  CAS  Google Scholar 

  53. L. Moradi, Z. Ataei, Green. Chem. Lett. Rev. 10, 380 (2017)

    Article  CAS  Google Scholar 

  54. B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 5004 (2012)

    Article  CAS  Google Scholar 

  55. M. Kidwai, A. Jahan, N.K. Mishra, Appl. Catal. A: General. 425–426, 35 (2012)

    Article  CAS  Google Scholar 

  56. G.D. Wang, X.N. Zhang, Z.H. Zhang, J. Heterocycl. Chem. 50, 61 (2013)

    Article  CAS  Google Scholar 

  57. S. Pradhan, B.G. Mishra, Mol. Catal. 446, 58 (2018)

    Article  CAS  Google Scholar 

  58. G.M. Ziarani, A. Badiei, S. Mousavi, N. Lashgari, A. Shahbazi, Chin. J. Catal. 33, 1832 (2012)

    Article  CAS  Google Scholar 

  59. Y. Li, H. Chen, C. Shi, D. Shi, S. Ji, J. Comb. Chem. 12, 231 (2010)

    Article  CAS  PubMed  Google Scholar 

  60. F.A. Tameh, J.S. Ghomi, M.M. Hashemi, H.S. Alavi, RSC. Adv. 6, 74802 (2016)

    Article  CAS  Google Scholar 

  61. F. Kamali, F. Shirini, J. Mol. Struct. 1227, 129654 (2021)

    Article  CAS  Google Scholar 

  62. M.N. Chen, J.Q. Di, J.M. Li, L.P. Mo, Z.H. Zhang, Tetrahedron 76, 131059 (2020)

    Article  CAS  Google Scholar 

  63. B. Sadeghi, M. Ghasem-Pirbaluti, P. Farokhi Nezhad, R. Abbasi Nezhad, Res. Chem. Intermed. 41, 4047 (2015)

    Article  CAS  Google Scholar 

  64. K. Niknam, P. Abolpour, Monatsh. Chem. 146, 683 (2015)

    Article  CAS  Google Scholar 

  65. B. Sadeghi, Z. Lasemi, R. Azimi, Orient. J. Chem. 31, 1175 (2015)

    Article  CAS  Google Scholar 

  66. M. Zhang, Q.Y. Fu, G. Gao, H.Y. He, Y. Zhang, Y.S. Wu, Z.H. Zhang, A.C.S. Sustain, Chem. Eng. 5, 6175 (2017)

    CAS  Google Scholar 

  67. Z. Lasemi, M. Tajbakhsh, H. Alinezhad, F. Mehrparvar, Res. Chem. Intermed. 46, 3667 (2020)

    Article  CAS  Google Scholar 

  68. R. Azimi, Z. Lasemi, A. Bagheri Hashkavayi, Lett. Org. Chem. 17, 268 (2020)

    Article  CAS  Google Scholar 

  69. R. Azimi, R. Baharfar, Can. J. Chem. 92, 1163 (2014)

    Article  CAS  Google Scholar 

  70. R. Baharfar, R. Azimi, M. Mohseni, J. Food. Sci. Technol. 52, 6777 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. E.C. Njagi, H. Huang, L. Stafford, H. Genuino, H.M. Galindo, J.B. Collins, G.E. Hoag, S.L. Suib, Langmuir 27, 264 (2011)

    Article  CAS  PubMed  Google Scholar 

  72. M. Dabiri, M. Bahramnejad, M. Baghbanzadeh, Tetrahedron 65, 9443 (2009)

    Article  CAS  Google Scholar 

  73. S. Zhu, S.I. Ji, Y. Zhang, Tetrahedron 63, 9365 (2007)

    Article  CAS  Google Scholar 

  74. K. Rad-Moghadam, L. Youseftabar-Miri, Tetrahedron 67, 5693 (2011)

    Article  CAS  Google Scholar 

  75. R.G. Chaudhary, J.A. Tanna, N.V. Gandhare, A.R. Rai, H.D. Juneja, Adv. Mater. Lett. 6, 990 (2015)

    Article  CAS  Google Scholar 

  76. G.S. Hari, Y.R. Lee, Synthesis 2010, 453 (2010)

    Article  CAS  Google Scholar 

  77. G. Shanthi, G. Subbulakshmi, P.T. Perumal, Tetrahedron 63, 2057 (2007)

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful to the Research Institute of Forests and Rangelands, Agricultural Research of Iran for partial support of this work.

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  1. Research Institute of Forests and Rangelands, Agricultural Research, Education and Extension Organization (AREEO), Tehran, Iran

    Razieh Azimi

  2. Department of Chemistry, South Tehran Branch, Islamic Azad University, Tehran, Iran

    Zahra Lasemi

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  1. Razieh Azimi
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Azimi, R., Lasemi, Z. Environmentally friendly synthesis of Ag/SiO2 nanoparticles using Thymus kotschyanus extract and its application as a green catalyst for synthesis of spirooxindoles. Res Chem Intermed 48, 1615–1630 (2022). https://doi.org/10.1007/s11164-022-04667-z

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