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Hexamethylenetetramine grafted layered double hydroxides as a novel and green heterogeneous ionic liquid catalyst for the synthesis of pyrido[2,3-d]pyrimidine derivatives

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Abstract

In this research layered double hydroxides functionalized with (3r,5r,7r)-1-(3-(triethoxysilyl)propyl)-1,3,5,7-tetraazaadamantan-1-ium chloride (LDHs–TPTAACl) as a novel, green, efficient and recyclable heterogeneous ionic liquid were synthesized and characterized by various methods, such as FT-IR, TGA, SEM, EDX, TEM and XRD. The mentioned catalyst was applied as a new ionic liquid catalyst for the one-pot three-component synthesis of a new class of pyrido[2,3-d]pyrimidine derivatives through combination of aromatic aldehydes, 2,4-thiazolidinedione and N,N-dimethyl-6-amino uracil using water as solvent in high to excellent yield and short reaction times. The LDHs–TPTAACl catalyst could be simply recycled and reused up to five continuous runs with no substantial structural change and loss of activity.

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References

  1. T. Cheng, D. Zhang, H. Li, G. Liu, Green Chem. 16, 3401 (2014)

    Article  CAS  Google Scholar 

  2. A. Nagaraju, B.J. Ramulu, G. Shukla, A. Srivastava, G.K. Verma, K. Raghuvanshi, M.S. Singh, Green Chem. 17, 950 (2015)

    Article  CAS  Google Scholar 

  3. R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)

    Article  CAS  Google Scholar 

  4. P. Ravichandiran, B. Lai, Y. Gu, Chem. Rec. 17, 142 (2017)

    Article  CAS  PubMed  Google Scholar 

  5. V. Polshettiwar, R.S. Varma, Green Chem. 12, 743 (2010)

    Article  CAS  Google Scholar 

  6. R. Liu, C. Dong, X. Liang, X. Wang, X. Hu, Chem, I. Ed. J. Org. Chem. 70, 729 (2005)

    Article  CAS  Google Scholar 

  7. G. Stavber, M. Zupan, M. Jereb, S. Stavber, Org. Lett. 6, 4973 (2004)

    Article  CAS  PubMed  Google Scholar 

  8. C.P. Mehnert, Chem. A Eur. J. 11, 50 (2005)

    Article  CAS  Google Scholar 

  9. A. Riisager, R. Fehrmann, S. Flicker, R. Van Hal, M. Haumann, P. Wasserscheid, Angew. Chemie Int. Ed. 44, 815 (2005)

    Article  CAS  Google Scholar 

  10. M.V. Reddy, N.T.K. Lien, G.C.S. Reddy, K.T. Lim, Y.T. Jeong, Green Chem. 18, 4228 (2016)

    Article  CAS  Google Scholar 

  11. J. He, M. Wei, B. Li, Y. Kang, D.G. Evans, X. Duan, Struct. Bond 89, 2006 (2006)

    Google Scholar 

  12. S. Yoon, J.-Y. Yun, J.-H. Lim, B. Yoo, J. Alloys Compd. 693, 964 (2017)

    Article  CAS  Google Scholar 

  13. M. Shao, R. Zhang, Z. Li, M. Wei, D.G. Evans, X. Duan, Chem. Commun. 51, 15880 (2015)

    Article  CAS  Google Scholar 

  14. H. Li, J. Li, C. Xu, P. Yang, D.H.L. Ng, P. Song, M. Zuo, J. Alloys Compd. 698, 852 (2017)

    Article  CAS  Google Scholar 

  15. J. Wang, R. Zhu, B. Gao, B. Wu, K. Li, X. Sun, H. Liu, S. Wang, Biomaterials 35, 466 (2014)

    Article  CAS  PubMed  Google Scholar 

  16. N.T. Thao, N.D. Trung, D. Van Long, Catal. Lett. 146, 918 (2016)

    Article  CAS  Google Scholar 

  17. E. Li, Z.P. Xu, V. Rudolph, Appl. Catal. B Environ. 88, 42 (2009)

    Article  CAS  Google Scholar 

  18. W.Y. Hernandez, F. Alic, A. Verberckmoes, P. Van Der Voort, J. Mater. Sci. 52, 628 (2017)

    Article  CAS  Google Scholar 

  19. M.S. Kwon, N. Kim, C.M. Park, J.S. Lee, K.Y. Kang, J. Park, S.K. Min, N. Kim, M.P. Cheon, S.L. Jae, Y.K. Kyung, J. Park, Org. Lett. 7, 1077 (2005)

    Article  CAS  PubMed  Google Scholar 

  20. M. Veeranarayana Reddy, G. Chandra Sekhar Reddy, N. Thi Kim Lien, D. W. Kim, Y. T. Jeong, Tetrahedron 4 (2017)

  21. S.R. Kanth, G.V. Reddy, P.H. Kishore, B.S. Rao, U.S.N. Murthy, Eur. J. Med. Chem. 41, 1011 (2006)

    Article  CAS  Google Scholar 

  22. E. Scapin, C. P. Frizzo, L. V. Rodrigues, G. C. Zimmer, R. A. Vaucher, M. R. Sagrillo, J. L. Giongo, C. A. M. Afonso, P. Rijo, N. Zanatta, H. G. Bonacorso, M. A. P. Martins, Med. Chem. Res. 1 (2017)

  23. R.K. Pavana, S. Choudhary, A. Bastian, M.A. Ihnat, R. Bai, E. Hamel, A. Gangjee, Bioorganic. Med. Chem. 25, 545 (2017)

    Article  CAS  Google Scholar 

  24. K. Avasthil, N. Gargl, T. Chandral, D.S. Bhakunil, P.P. Gupta, R. C. Srimal. 1502, 585 (1993)

    Google Scholar 

  25. A. Haleel, D. Mahendiran, V. Veena, N. Sakthivel, A.K. Rahiman, Mater. Sci. Eng. C 68, 366 (2016)

    Article  CAS  Google Scholar 

  26. A.Y. Kots, B.-K. Choi, M.E. Estrella-Jimenez, C.A. Warren, S.R. Gilbertson, R.L. Guerrant, F. Murad, Proc. Natl. Acad. Sci. USA 105, 8440 (2008)

    Article  PubMed  Google Scholar 

  27. D.R. Huron, M.E. Gorre, A.J. Kraker, C.L. Sawyers, N. Rosen, M.M. Moasser, Clin. Cancer Res. 9, 1267 (2003)

    CAS  PubMed  Google Scholar 

  28. A. Gangjee, O. Adair, S.F. Queener, J. Med. Chem. 42, 2447 (1999)

    Article  CAS  PubMed  Google Scholar 

  29. D.C. Kim, Y.R. Lee, B.-S. Yang, K.J. Shin, D.J. Kim, B.Y. Chung, K.H. Yoo, Eur. J. Med. Chem. 38, 525 (2003)

    Article  CAS  PubMed  Google Scholar 

  30. L. Le Corre, A.-L. Girard, J. Aubertin, F. Radvanyi, C. Benoist-Lasselin, A. Jonquoy, E. Mugniery, L. Legeai-Mallet, P. Busca, Y. Le Merrer, Org. Biomol. Chem. 8, 2164 (2010)

    Article  CAS  PubMed  Google Scholar 

  31. G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, Tetrahedron Lett. 53, 399 (2012)

    Article  CAS  Google Scholar 

  32. J. Rangel, C. Díaz-Uribe, A. Rodriguez-Serrano, X. Zarate, Y. Serge, W. Vallejo, M. Nogueras, J. Trilleras, J. Quiroga, J. Tatchen, J. Cobo, J. Mol. Struct. 1137, 431 (2017).

    Article  CAS  Google Scholar 

  33. M. Fattahi, A. Davoodnia, M. Pordel, Russ. J. Gen. Chem. 87, 863 (2017)

    Article  CAS  Google Scholar 

  34. R. Ghorbani-Vaghei, N. Sarmast, J. Mahmoodi, Appl. Organomet. Chem. 1 (2016)

  35. R. Ghorbani-Vaghei, A. Shahriari, Z. Salimi, S. Hajinazari, RSC Adv. 5, 3665 (2015)

    Article  CAS  Google Scholar 

  36. S. Jin, H. Zhang, K. Xu, X. Ye, Y. Zhang, Y. Fang, D. Wang, Polyhedron 95, 108 (2015)

    Article  CAS  Google Scholar 

  37. J.W. Lee, J.M. Ko, J.D. Kim, Electrochim. Acta 85, 459 (2012)

    Article  CAS  Google Scholar 

  38. A.M. Kirillov, Coord. Chem. Rev. 255, 1603 (2011)

    Article  CAS  Google Scholar 

  39. D.M. Yufanyi, A.M. Ondoh, J. Foba-Tendo, K.J. Mbadcam, Am. J. Chem. 5, 1 (2015)

    Article  CAS  Google Scholar 

  40. M.V. Reddy, N.T.K. Lien, G.C.S. Reddy, K.T. Lim, Y.T. Jeong, Green Chem. 18, 4228 (2016)

    Article  CAS  Google Scholar 

  41. J. Plank, Z. Dai, P.R. Andres, Mater. Lett. 60, 3614 (2006)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors wish to thank the Research Council of Bu-Ali Sina University for financial support to carry out this research.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 65174, Iran

    Ramin Ghorbani-Vaghei & Narges Sarmast

Authors
  1. Ramin Ghorbani-Vaghei
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  2. Narges Sarmast
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Correspondence to Ramin Ghorbani-Vaghei.

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Ghorbani-Vaghei, R., Sarmast, N. Hexamethylenetetramine grafted layered double hydroxides as a novel and green heterogeneous ionic liquid catalyst for the synthesis of pyrido[2,3-d]pyrimidine derivatives. Res Chem Intermed 44, 4483–4501 (2018). https://doi.org/10.1007/s11164-018-3399-8

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