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Copper (0) nanoparticles onto silica: A stable and facile catalyst for one-pot synthesis of 2,2′-arylmethylene bis (3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) via cascade Knoevenagel/Michael reaction

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Abstract

Solid supported copper (0) nanoparticles were prepared by physical adsorption of copper (0) nanoparticles (synthesized through bottom-up approach) on the solid supports such as silica, HAP, cellulose and basic alumina. Studies comparing these supported catalysts were done with the synthesis of arylmethylene-bis-(3-hydroxy-2-cyclohexene-1-one) via the cascade Knoevenagel/Michael reaction. The highly efficient catalyst was characterized by spectroscopic techniques like XPS, TGA, EDX, SEM, TEM and AAS. The biological importance of arylmethylene-bis-(3-hydroxy-2-cyclohexene-1-one) enforced us to synthesize these compounds catalytically using solid supported copper (0) nanopartcles.

SiO2-Cu(0) nanoparticles have been used as catalyst for the synthesis of 2,2′- arylmethylene-bis-(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) via cascade Knoevenagel/ Michael reaction. The heterogeneity of the catalyst has been confirmed by post-characterization techniques like TEM micrographs and recyclability test.

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References

  1. Jung D H, Lee Y R, Kim S H and Lyoo W S 2009 Bull. Korean Chem. Soc. 30 1989

    Article  CAS  Google Scholar 

  2. Maharvi G M, Ali S, Riaz N, Afza N, Malik A, Ashraf M, Iqbal L, Lateef M and Enzyme J 2008 Inhib. Med. Chem. 23 62

  3. Khan K M, Maharvi G M, Khan M T H, Shaikh A J, Perveen S, Mild S B and Choudhary M I 2006 Bioorg. Med. Chem. 14 344

  4. Kantevari S, Bantu R and Nagarapu L 2007 J. Mol. Catal. A: Chem. 269 53

    Article  CAS  Google Scholar 

  5. Fan X S, Li Y Z, Zhang X Y, Hu X Y and Wang J 2005 J. Chin. Chem. Lett. 16 897

    CAS  Google Scholar 

  6. Kidwai M, Bansal V, Mothsra P, Saxena S, Somvanshi R K, Dey S and Singh T P 2007 J. Mol. Catal. A: Chem. 268 76

    Article  CAS  Google Scholar 

  7. Seyyedhamzeh M, Mirzaei P and Bazgir A 2008 Dyes Pigm. 76 836

    Article  CAS  Google Scholar 

  8. Das B, Thirupathi P, Reddy K R, Ravikanth B and Nagarapu L 2007 Catal. Commun. 8 535

    Article  CAS  Google Scholar 

  9. Zhang Z H and Liu Y H 2008 Catal. Commun. 9 1715

    Article  CAS  Google Scholar 

  10. Shaterian H R, Hosseinian A and Ghashang M 2008 Phosphorus, Sulfur Silicon Relat. Elem. 183 3136

    Article  CAS  Google Scholar 

  11. Jin T S, Zhang J S, Wang A Q and Li T S 2005 Synth. Commun. 35 2339

  12. Shakibaei G I, Mirzaei P and Bazgir A 2007 Appl. Catal. A: Gen. 325 188

    Article  CAS  Google Scholar 

  13. John A, Yadav P J P and Palaniappan S 2006 J. Mol. Catal. A: Chem. 248 121

    Article  CAS  Google Scholar 

  14. Jin T S, Zhang J S, Wang A Q and Li T S 2006 Ultrason. Sonochem. 13 220

    Article  CAS  Google Scholar 

  15. Das B, Thirupathi P, Mahender I, Reddy V S and Rao T K 2006 J. Mol. Catal. A: Chem. 247 233

  16. Song G, Wang B, Luo H and Yang L 2007 Catal. Commun. 8 673

    Article  CAS  Google Scholar 

  17. Darviche F, Balalaie S, Chadegani F and Salehi P 2007 Synth. Commun. 37 1059

    Article  CAS  Google Scholar 

  18. Shi D Q, Zhuang Q Y, Chen J, Wang X S, Tu S J and Hu H W 2003 Chin. J. Org. Chem. 23 694

    CAS  Google Scholar 

  19. Ma J J, Zhou X, Zhang X H, Wang C, Wang Z, Li J C and Li Q 2007 Aust. J. Chem. 60 146

    Article  CAS  Google Scholar 

  20. Kantevari S, Bantu R and Nagarapu L 2006 ARKIVOC xvi 136

  21. Dabiri M, Baghbanzadeh M and Arzroomchilar E 2008 Catal. Commun. 9 939

    Article  CAS  Google Scholar 

  22. Zhang H X, Siegert U, Liu R and Cai W B 2009 Nanoscale Res. Lett. 4 705

    Article  CAS  Google Scholar 

  23. Kumari S, Shekhar A and Pathak D 2014 Chem. Sci. Trans. 3 652

    Google Scholar 

  24. Khurana J M and Vij K 2012 J. Chem. Sci. 124 907

    Article  CAS  Google Scholar 

  25. Sheldrick G M 2008 Acta Cryst. A64 112

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Jammu, Jammu, 180 006, India

    MANJULLA GUPTA & MONIKA GUPTA

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  1. MANJULLA GUPTA
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  2. MONIKA GUPTA
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Correspondence to MONIKA GUPTA.

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Supplementary Information (SI)

Supplementary Information related to characterization of SiO2-Cu(0), spectral details of some compounds and 1H NMR of selected compounds are available at www.ias.ac.in/chemsci.

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GUPTA, M., GUPTA, M. Copper (0) nanoparticles onto silica: A stable and facile catalyst for one-pot synthesis of 2,2′-arylmethylene bis (3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) via cascade Knoevenagel/Michael reaction. J Chem Sci 128, 849–854 (2016). https://doi.org/10.1007/s12039-016-1080-6

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  • DOI: https://doi.org/10.1007/s12039-016-1080-6

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