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A Simple and Highly Versatile Procedure for the Knoevenagel Condensation Promoted by an Efficient, Eco-Friendly, and Recyclable nano-ZnO Catalyst

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Abstract

A simple, highly versatile, and efficient protocol for the synthesis of substituted olefins from various aromatic aldehydes and active methylene compounds by Knoevenagel condensation using an efficient, eco-friendly, and recyclable nano-ZnO catalyst in ethanol at a moderate temperature was developed. Due to its large surface area, the nano-ZnO catalyst exhibited an excellent catalytic activity. The advantages of the method included milder conditions, short reaction times, and easy work-up and purification of products by non-chromatographic methods. The catalysts can be recovered for subsequent reactions and reused without any appreciable loss of efficiency.

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REFERENCES

  1. Ryabukhin, S.V., Plaskon, A.S., Volochnyuk, D.M., Pipko, S.E., Shivanyuk, A.N., and Tolmachev, A.A., J. Comb. Chem., 2007, vol. 9, p. 1073. https://doi.org/10.1021/cc070073f

    Article  CAS  PubMed  Google Scholar 

  2. Tietze, L.F. and Saling, P., Synlett, 1992, p. 281. https://doi.org/10.1055/s-1992-21339

  3. Kim, I., Kim, S.G., Choi, J., and Lee, G.H., Tetrahedron, 2008, vol. 64, p. 664. https://doi.org/10.1016/j.tet.2007.11.036

    Article  CAS  Google Scholar 

  4. Tietze, L.F., Chem. Rev., 1996, vol. 96, p. 115. https://doi.org/10.1021/cr950027e

    Article  CAS  PubMed  Google Scholar 

  5. Basavaiah, D., Rao, A.J., and Satyanarayana, T., Chem,Rev., 2003, vol. 103, p. 811. https://doi.org/10.1021/cr010043d

    Article  CAS  Google Scholar 

  6. Sammelson, D.E. and Kurth, M.J., Chem. Rev., 2001, vol. 101, p. 137. https://doi.org/10.1021/cr000086e

    Article  CAS  PubMed  Google Scholar 

  7. Huddleston, R.R. and Krische, M.J., Synlett, 2003, vol. 1, p. 12. https://doi.org/10.1055/S-2003-36213

    Article  Google Scholar 

  8. Gibson, S.E. and Stevenazzi, A., Angew. Chem. Int.Ed., 2003, vol. 42, p. 1800. https://doi.org/10.1002/1nie.200200547

    Article  CAS  Google Scholar 

  9. Moreno-Monas, M. and Pleixats, R., Acc. Chem. Res., 2003, vol. 36, p. 638. https://doi.org/10.1021/ar020267y

    Article  CAS  Google Scholar 

  10. Asiri, A.M., Dyes Pigm., 1999, vol. 42, p. 209. https://doi.org/10.1016/S0143-7208(99)00024-8

    Article  CAS  Google Scholar 

  11. Ballini, R. and Bosica, G. J., J. Org. Chem., 1997, vol. 62, p. 425. https://doi.org/10.1021/jo961201h

    Article  CAS  PubMed  Google Scholar 

  12. Tang, Z., Yang, Z.-H., Chen, X.-H., Cun, L.-F., Mi, A.-Q., Jiang, Y.-Zh., and Gong, L.-Z., J. Am. Chem. Soc., 2005, vol. 127, p. 9285. https://doi.org/10.1021/ja0510156

    Article  CAS  PubMed  Google Scholar 

  13. Whitesides, G.M., Small, 2005, vol. 1, p. 172. https://doi.org/10.1002/smll.200400130

    Article  CAS  PubMed  Google Scholar 

  14. Varma, R.S., Green Chem., 2014, vol. 16, p. 2027. https://doi.org/10.1039/C3GC42640H

    Article  CAS  Google Scholar 

  15. Chng, L.L., Earthodiyil, N., and Ying, J.Y., Acc. Chem.Res., 2013, vol. 46, p. 1825. https://doi.org/10.1021/ar300197s

    Article  CAS  PubMed  Google Scholar 

  16. Hattori, H., Chem. Rev., 1995, vol. 95, p. 537. https://doi.org/10.1021/cr00035a005

    Article  CAS  Google Scholar 

  17. Canning, A.S., Jackson, S.D., McLeod, E., and Vass, E.M., Appl. Catal. A, 2005, vol. 289, p. 59. https://doi.org/10.1016/j.apcata.2005.04.019

    Article  CAS  Google Scholar 

  18. Winter, F., Van Dillen, A.J., and De Jong, K.P., Chem.Commun., 2005, vol. 31, p. 3977. https://doi.org/10.1039/B506173C

    Article  Google Scholar 

  19. Garro, R., Navarro, M.T., Primo, J., and Corma, A., J. Catal., 2005, vol. 233, p. 342. https://doi.org/10.1016/j.jcat.2005.04.035

    Article  CAS  Google Scholar 

  20. Smahi, A., Solhy, A., El Badaoui, H., Amoukal, A., Tikad, A., Maizi, M., and Sebti, S., Appl. Catal. A, 2003, vol. 250, p. 151. https://doi.org/10.1016/S0926-860X(03)00254-0

    Article  CAS  Google Scholar 

  21. Wada, S. and Suzuki, H., Tetrahedron Lett., 2003, vol. 44, p. 399. https://doi.org/10.1016/S0040-4039(02)02431-0

    Article  CAS  Google Scholar 

  22. Kantam, M.L., Choudary, B.M., Reddy, C.V., Rao, K.K., and Figueras, F., Chem. Commun., 1998, vol. 9, p. 1033. https://doi.org/10.1039/a707874i

    Article  Google Scholar 

  23. Akutu, K., Kabashima, H., Seki, T., and Hattori, H., Appl. Catal. A, 2003, vol. 247, p. 65. https://doi.org/10.1016/S0926-860X(03)00124-8

    Article  CAS  Google Scholar 

  24. Choudary, B.M., Kantam, M.L., Reddy, C.V., Koteswara Rao, K., and Figueras, F., Green Chem., 1999, vol. 1, p. 187. https://doi.org/10.1039/a904075g

    Article  CAS  Google Scholar 

  25. Utting, K.A. and Macquarrie, D.J., New J. Chem., 2000, vol. 24, p. 591. https://doi.org/10.1039/b002424o

    Article  CAS  Google Scholar 

  26. Lai, S.M., Ng, C.P., Martin-Arnade, R., and Yeung, K.L., Microporous Mesoporous Mater., 2003, vol. 66, p. 239. https://doi.org/10.1016/j.micromeso.2003.09.014

    Article  CAS  Google Scholar 

  27. Kossir, A. and Qumimoum, H., Catal. Commun., 2002, vol. 3, p. 335. https://doi.org/10.1016/S1566-7367(02)00137-1

    Article  Google Scholar 

  28. Calloway, N.O. and Green, L.D., J. Am.Chem. Soc., 1937, vol. 59, 809. https://doi.org/10.1021/ja01284a011

  29. Szell, T. and Sohar, I., Can. J. Chem., 1969, vol. 47, p. 1254. https://doi.org/10.1139/v69-207

    Article  CAS  Google Scholar 

  30. Irice, K. and Watanabe, K., Bull. Chem. Soc. Jpn., 1980, vol. 53, p. 1366. https://doi.org/10.1246/bcsj.53.1366

    Article  Google Scholar 

  31. Mazza, L. and Guaram, A., Synthesis, 1980, vol. 1980, p. 41. https://doi.org/10.1055/s-1980-28916

    Article  Google Scholar 

  32. Nakano, T., Irifune, S., Umano, S., Inada, A., Ishii, Y., and Ogawa, M., J. Org. Chem., 1987, vol. 52, p. 2239. https://doi.org/10.1021/jo00387a025

    Article  CAS  Google Scholar 

  33. Iranpoor, N. and Kazemi, F., Tetrahedron, 1998, vol. 54, p. 9475. https://doi.org/10.1016/S0040-4020(98)00575-4

    Article  CAS  Google Scholar 

  34. Poor Heravi, M.R., J. Iran. Chem. Soc., 2009, vol. 6, p. 483. https://doi.org/10.1007/BF03246525

    Article  Google Scholar 

  35. Pacholski, C., Kornowski, A., and Weller, H., Angew.Chem., 2002, vol. 41, p. 1188. https://doi.org/10.1002/1521-3773(20020402)41:7<1188::AID-ANIE1188>3.0.CO;2-5

    Article  CAS  Google Scholar 

  36. Gayen, R.N., Bhar, R., and Pal, A.K., Ind. J. PureAppl. Phys., 2010, vol. 48, p. 385. http://hdl.handle.net/123456789/9041

    CAS  Google Scholar 

  37. Hosseini-Sarvari, M., Catal. Lett., 2011, vol. 141, p. 347. https://doi.org/10.1007/s10562-010-0489-7

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors would like to express their gratitude to King Khalid University, Saudi Arabia, for providing administrative and technical support. The research has no funding support and was carried out as part of employment (employee King Khalid University).

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, 61421, Abha, Saudi Arabia

    S. Tasqeeruddin

  2. Department of Pharmacology, College of Pharmacy, King Khalid University, 61421, Abha, Saudi Arabia

    Ya. I. Asiri

  3. Department of Chemistry, College of Science, King Khalid University, 61421, Abha, Saudi Arabia

    M. M. Alam

  4. School of pharmacy and medical sciences, Singhania University, Pacheri Bari, Jhunjhunu, 333515, Rajasthan, India

    S. Sh. Sulthana

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  1. S. Tasqeeruddin
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Correspondence to S. Tasqeeruddin.

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Tasqeeruddin, S., Asiri, Y.I., Alam, M.M. et al. A Simple and Highly Versatile Procedure for the Knoevenagel Condensation Promoted by an Efficient, Eco-Friendly, and Recyclable nano-ZnO Catalyst. Russ J Org Chem 56, 315–321 (2020). https://doi.org/10.1134/S1070428020020220

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