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Research on Chemical Intermediates

, Volume 44, Issue 7, pp 4483–4501 | Cite as

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

  • Ramin Ghorbani-Vaghei
  • Narges Sarmast
Article
  • 70 Downloads

Abstract

In this research layered double hydroxides functionalized with (3r,5r,7r)-1-(3-(triethoxysilyl)propyl)-1,3,5,7-tetraazaadamantan-1-ium chloride (LDHsTPTAACl) 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 LDHsTPTAACl catalyst could be simply recycled and reused up to five continuous runs with no substantial structural change and loss of activity.

Graphical Abstract

Keywords

LDHs Green chemistry Ionic liquid Pyrido[2,3-d]pyrimidine Uracil 

Notes

Acknowledgements

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

Supplementary material

11164_2018_3399_MOESM1_ESM.doc (1.1 mb)
Supplementary material 1 (DOC 1159 kb)

References

  1. 1.
    T. Cheng, D. Zhang, H. Li, G. Liu, Green Chem. 16, 3401 (2014)CrossRefGoogle Scholar
  2. 2.
    A. Nagaraju, B.J. Ramulu, G. Shukla, A. Srivastava, G.K. Verma, K. Raghuvanshi, M.S. Singh, Green Chem. 17, 950 (2015)CrossRefGoogle Scholar
  3. 3.
    R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)CrossRefGoogle Scholar
  4. 4.
    P. Ravichandiran, B. Lai, Y. Gu, Chem. Rec. 17, 142 (2017)CrossRefGoogle Scholar
  5. 5.
    V. Polshettiwar, R.S. Varma, Green Chem. 12, 743 (2010)CrossRefGoogle Scholar
  6. 6.
    R. Liu, C. Dong, X. Liang, X. Wang, X. Hu, Chem, I. Ed. J. Org. Chem. 70, 729 (2005)CrossRefGoogle Scholar
  7. 7.
    G. Stavber, M. Zupan, M. Jereb, S. Stavber, Org. Lett. 6, 4973 (2004)CrossRefGoogle Scholar
  8. 8.
    C.P. Mehnert, Chem. A Eur. J. 11, 50 (2005)CrossRefGoogle Scholar
  9. 9.
    A. Riisager, R. Fehrmann, S. Flicker, R. Van Hal, M. Haumann, P. Wasserscheid, Angew. Chemie Int. Ed. 44, 815 (2005)CrossRefGoogle Scholar
  10. 10.
    M.V. Reddy, N.T.K. Lien, G.C.S. Reddy, K.T. Lim, Y.T. Jeong, Green Chem. 18, 4228 (2016)CrossRefGoogle Scholar
  11. 11.
    J. He, M. Wei, B. Li, Y. Kang, D.G. Evans, X. Duan, Struct. Bond 89, 2006 (2006)Google Scholar
  12. 12.
    S. Yoon, J.-Y. Yun, J.-H. Lim, B. Yoo, J. Alloys Compd. 693, 964 (2017)CrossRefGoogle Scholar
  13. 13.
    M. Shao, R. Zhang, Z. Li, M. Wei, D.G. Evans, X. Duan, Chem. Commun. 51, 15880 (2015)CrossRefGoogle Scholar
  14. 14.
    H. Li, J. Li, C. Xu, P. Yang, D.H.L. Ng, P. Song, M. Zuo, J. Alloys Compd. 698, 852 (2017)CrossRefGoogle Scholar
  15. 15.
    J. Wang, R. Zhu, B. Gao, B. Wu, K. Li, X. Sun, H. Liu, S. Wang, Biomaterials 35, 466 (2014)CrossRefGoogle Scholar
  16. 16.
    N.T. Thao, N.D. Trung, D. Van Long, Catal. Lett. 146, 918 (2016)CrossRefGoogle Scholar
  17. 17.
    E. Li, Z.P. Xu, V. Rudolph, Appl. Catal. B Environ. 88, 42 (2009)CrossRefGoogle Scholar
  18. 18.
    W.Y. Hernandez, F. Alic, A. Verberckmoes, P. Van Der Voort, J. Mater. Sci. 52, 628 (2017)CrossRefGoogle Scholar
  19. 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)CrossRefGoogle Scholar
  20. 20.
    M. Veeranarayana Reddy, G. Chandra Sekhar Reddy, N. Thi Kim Lien, D. W. Kim, Y. T. Jeong, Tetrahedron 4 (2017)Google Scholar
  21. 21.
    S.R. Kanth, G.V. Reddy, P.H. Kishore, B.S. Rao, U.S.N. Murthy, Eur. J. Med. Chem. 41, 1011 (2006)CrossRefGoogle Scholar
  22. 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)Google Scholar
  23. 23.
    R.K. Pavana, S. Choudhary, A. Bastian, M.A. Ihnat, R. Bai, E. Hamel, A. Gangjee, Bioorganic. Med. Chem. 25, 545 (2017)CrossRefGoogle Scholar
  24. 24.
    K. Avasthil, N. Gargl, T. Chandral, D.S. Bhakunil, P.P. Gupta, R. C. Srimal. 1502, 585 (1993)Google Scholar
  25. 25.
    A. Haleel, D. Mahendiran, V. Veena, N. Sakthivel, A.K. Rahiman, Mater. Sci. Eng. C 68, 366 (2016)CrossRefGoogle Scholar
  26. 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)CrossRefGoogle Scholar
  27. 27.
    D.R. Huron, M.E. Gorre, A.J. Kraker, C.L. Sawyers, N. Rosen, M.M. Moasser, Clin. Cancer Res. 9, 1267 (2003)Google Scholar
  28. 28.
    A. Gangjee, O. Adair, S.F. Queener, J. Med. Chem. 42, 2447 (1999)CrossRefGoogle Scholar
  29. 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)CrossRefGoogle Scholar
  30. 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)CrossRefGoogle Scholar
  31. 31.
    G.K. Verma, K. Raghuvanshi, R. Kumar, M.S. Singh, Tetrahedron Lett. 53, 399 (2012)CrossRefGoogle Scholar
  32. 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).CrossRefGoogle Scholar
  33. 33.
    M. Fattahi, A. Davoodnia, M. Pordel, Russ. J. Gen. Chem. 87, 863 (2017)CrossRefGoogle Scholar
  34. 34.
    R. Ghorbani-Vaghei, N. Sarmast, J. Mahmoodi, Appl. Organomet. Chem. 1 (2016)Google Scholar
  35. 35.
    R. Ghorbani-Vaghei, A. Shahriari, Z. Salimi, S. Hajinazari, RSC Adv. 5, 3665 (2015)CrossRefGoogle Scholar
  36. 36.
    S. Jin, H. Zhang, K. Xu, X. Ye, Y. Zhang, Y. Fang, D. Wang, Polyhedron 95, 108 (2015)CrossRefGoogle Scholar
  37. 37.
    J.W. Lee, J.M. Ko, J.D. Kim, Electrochim. Acta 85, 459 (2012)CrossRefGoogle Scholar
  38. 38.
    A.M. Kirillov, Coord. Chem. Rev. 255, 1603 (2011)CrossRefGoogle Scholar
  39. 39.
    D.M. Yufanyi, A.M. Ondoh, J. Foba-Tendo, K.J. Mbadcam, Am. J. Chem. 5, 1 (2015)CrossRefGoogle Scholar
  40. 40.
    M.V. Reddy, N.T.K. Lien, G.C.S. Reddy, K.T. Lim, Y.T. Jeong, Green Chem. 18, 4228 (2016)CrossRefGoogle Scholar
  41. 41.
    J. Plank, Z. Dai, P.R. Andres, Mater. Lett. 60, 3614 (2006)CrossRefGoogle Scholar

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© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryBu-Ali Sina UniversityHamedanIran

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