Research on Chemical Intermediates

, Volume 44, Issue 5, pp 3337–3348 | Cite as

Metal free green protocol for the synthesis of bis-spiro piperidine and pyrimidine derivatives

Article
  • 63 Downloads

Abstract

A highly efficient one-pot three-component synthesis of bis-spiro piperidine and pyrimidine derivatives has been reported by performing the reaction of formaldehyde, aromatic aniline and 1,3-dicarbonyl compounds. This reaction was carried out at room temperature in 2,2,2-trifluoroethanol (TFE) as a recyclable reaction medium under the metal free condition. The strong hydrogen donor ability and acidic property of TFE plays a key role in accelerating the rate of reaction and initiates the reaction smoothly. The advantageous features of this method are a mild reaction condition, no column chromatographic purification, and high yield of products and recyclability of TFE.

Graphical Abstract

Keywords

2,2,2-Trifluoroethanol Bis-spiro piperidine 1,3-Diaryl-hexahydropyrimidine Multicomponent reaction Green synthesis Reusability 

Notes

Acknowledgements

We gratefully acknowledge the financial support from the Department of Science and Technology and University Grants Commission, New Delhi, India.

Supplementary material

11164_2018_3310_MOESM1_ESM.docx (14 kb)
Supplementary material 1 (DOCX 13 kb)

References

  1. 1.
    I.T. Horvath, P.T. Anastas, Chem. Rev. 107, 2167 (2007)CrossRefGoogle Scholar
  2. 2.
    A. Dandia, R. Sigh, J. Joshi, S. Kumari, J. Fluor. Chem. 156, 238 (2013)CrossRefGoogle Scholar
  3. 3.
    H. Alinezhad, M. Taibakhsh, M. Zare, J. Fluor. Chem. 132, 995 (2011)CrossRefGoogle Scholar
  4. 4.
    M. Daryabhari, S. Khaksar, J. Mol. Liq. 198, 263 (2014)CrossRefGoogle Scholar
  5. 5.
    S. Rostanmia, E. Doustkhah, Tetrahedron Lett. 55, 2508 (2014)CrossRefGoogle Scholar
  6. 6.
    K. De, J. Legros, B. Crousse, D. Bonnet-Delpon, J. Org. Chem. 74, 6260 (2009)CrossRefGoogle Scholar
  7. 7.
    S. Rashmi, N. Sandhya, B. Raghava, M. Kumara, K. Mantelingu, K. Rangappa, Synth. Commun. 43, 424 (2012)CrossRefGoogle Scholar
  8. 8.
    E. Doustkhah, S. Rostamnia, A. Hassankhani, J. Porous Mater. 23, 549 (2016)CrossRefGoogle Scholar
  9. 9.
    S. Rostamnia, E. Doustkhah, Synlett 26(10), 1345 (2015)CrossRefGoogle Scholar
  10. 10.
    S. Khaksar, J. Fluor. Chem. 172, 51 (2015)CrossRefGoogle Scholar
  11. 11.
    S. Rostamnia, E. Doustkhah, A. Nuri, J. Fluor. Chem. 153, 1 (2013)CrossRefGoogle Scholar
  12. 12.
    S. Rostamnia, E. Doustkhah, K. Bahrami, S. Amini, J. Mol. Liq. 207, 334 (2015)CrossRefGoogle Scholar
  13. 13.
    S. Rostamnia, A. Zabardasti, J. Fluor. Chem. 144, 69 (2012)CrossRefGoogle Scholar
  14. 14.
    I. Shuklov, N. Durrovina, A. Borner, Synthesis 19, 2925 (2007)CrossRefGoogle Scholar
  15. 15.
    R. Cioc, E. Ruitzer, R. Orru, Green Chem. 16, 2958 (2014)CrossRefGoogle Scholar
  16. 16.
    X. Xin, Y. Wang, S. Kumar, X. Liu, Y. Lin, D. Dong, Org. Biomol. Chem. 8, 3078 (2010)CrossRefGoogle Scholar
  17. 17.
    A. Jadhav, S. Balve, K. Lim, Y. Jeong, Tetrahedron 73, 2806 (2017)CrossRefGoogle Scholar
  18. 18.
    R. Ghahremanzadeh, G. Shakibaei, S. Ahadi, A. Bazgir, J. Comb. Chem. 12, 191 (2010)CrossRefGoogle Scholar
  19. 19.
    J. Li, N. Wu, Y. Tian, J. Zhang, S. Wu, A.C.S. Med, Chem. Lett. 4, 806 (2013)Google Scholar
  20. 20.
    N. Kozlov, A. Kadutskii, Tetrahedron Lett. 49, 3875 (2008)Google Scholar
  21. 21.
    L. Ye, Y. Tian, Z. Li, H. Jin, Z. Zhu, S. Wan, J. Zhang, P. Yu, J. Zhang, S. Wu, Eur. J. Med. Chem. 50, 370 (2012)CrossRefGoogle Scholar
  22. 22.
    S. Padvi, Y. Tayde, Y. Wagh, D. Dalal, Chin. Chem. Lett. 2, 714 (2016)CrossRefGoogle Scholar
  23. 23.
    J. Vieges, S. Bolzani, M. Furlan, J. Barreiro, C. Young, D. Tomazela, N. Eberlin, J. Nat. Prod. 67, 908 (2004)CrossRefGoogle Scholar
  24. 24.
    H. Bin, M. Crider, A. Stables, Eur. J. Med. Chem. 36, 265 (2001)CrossRefGoogle Scholar
  25. 25.
    R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, J. Med. Chem. 51, 5731 (2008)CrossRefGoogle Scholar
  26. 26.
    M. Mishra, S. Pandey, V. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17, 625 (2009)CrossRefGoogle Scholar
  27. 27.
    R. Weis, K. Schweiger, J. Faist, E. Rajkovic, A. Kungl, W. Fabin, W. Schunack, W. Seebacher, Bioorg. Med. Chem. 16, 10326 (2008)CrossRefGoogle Scholar
  28. 28.
    S. Petit, J. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, Eur. J. Med. Chem. 26, 19 (1991)CrossRefGoogle Scholar
  29. 29.
    Y. Zhou, V. Gregor, B. Ayida, G. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J. Froelich, S. Fish, S. Webber, D. Wall, Bioorg. Med. Chem. Lett. 17, 1206 (2007)CrossRefGoogle Scholar
  30. 30.
    C. Mukhopadhyay, S. Rana, R.J. Butcher, Tetrahedron Lett. 52, 4153 (2011)CrossRefGoogle Scholar
  31. 31.
    A. Dandia, A. Jain, S. Sharma, Tetrahedron Lett. 53, 5270 (2012)CrossRefGoogle Scholar
  32. 32.
    A.B. Atar, Y.T. Jeong, Tetrahedron Lett. 54, 1302 (2013)CrossRefGoogle Scholar
  33. 33.
    S. Ray, S. Bhaumik, B. Banerjee, P. Manna, C. Mukhopadhyay, Monatsh. Chem. Chem. Mon. 146, 1881 (2015)CrossRefGoogle Scholar
  34. 34.
    M. Mousavi, H. Gharari, M. Maghsoodiou, N. Hazeri, Res. Chem. Intermed. 42, 3875 (2016)CrossRefGoogle Scholar
  35. 35.
    P. Chidurla, V. Jetti, J. Meshram, J. Heterocycl. Chem. 53, 389 (2016)CrossRefGoogle Scholar
  36. 36.
    T. Lohar, S. Jadhav, A. Kumbhar, A. Mane, R. Salunkhe, Res. Chem. Intermed. 42, 5329 (2016)CrossRefGoogle Scholar
  37. 37.
    N. Ahmed, Z. Siddiqui, A.C.S. Sustain, Chem. Eng. 3, 1701 (2015)Google Scholar
  38. 38.
    F. Janati, M. Heravi, A. Mirshokraie, J. Chem. 2013, 1 (2013)Google Scholar
  39. 39.
    A. Dandia, A. Jain, S. Sharma, RSC Adv. 3, 2924 (2013)CrossRefGoogle Scholar

Copyright information

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

Authors and Affiliations

  1. 1.Department of ChemistryShivaji UniversityKolhapurIndia

Personalised recommendations