Efficient synthesis of 4H-pyran derivatives using a polymeric catalyst based on PVP

Abstract

A one-pot efficient method for the synthesis of 4H-pyran derivatives has been developed through a multi-component reaction of aldehydes, malononitrile, and 1,3-cyclic diketones using poly(vinylpyrrolidonium) hydrogen sulfate ([PVPH]HSO4) as a heterogeneous and reusable catalyst. The synthesized polymeric catalyst has fully been characterized by Fourier transform infrared spectra, X-ray diffraction, scanning electron microscopy, thermal gravimetric analysis, Hammett acidity (H0), and pH analysis, which expose of the polymeric catalyst. This procedure has the advantages of operational simplicity, mild conditions, easy work-up, short reaction times, high yields of the products, and reusability of the catalyst.

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References

  1. 1.

    M. Darbarwar, V. Sundaramurthy, Synthesis 5, 337 (1982)

    Article  Google Scholar 

  2. 2.

    T.S. Jin, R.Q. Zhao, T.S. Li, Arkivoc 11, 176 (2006)

    Google Scholar 

  3. 3.

    D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44, 3805 (2009)

    CAS  Article  Google Scholar 

  4. 4.

    A. Shaabani, M. Mohammadpour Amini, S. Ghasemi, R. Ghadari, A.H. Rezayan, Y. Fazaeli, S. Feizi, Chem. Pharm. Bull. 58, 270 (2010)

    CAS  Article  Google Scholar 

  5. 5.

    E.R. Bissell, A.R. Mitchell, R.E. Smith, J. Org. Chem. 45, 2283 (1980)

    CAS  Article  Google Scholar 

  6. 6.

    E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, F.M.A. El-Taweel, Heterocycles 26, 903 (1987)

    CAS  Article  Google Scholar 

  7. 7.

    L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)

    CAS  Article  Google Scholar 

  8. 8.

    A. Nefzi, J.M. Ostresh, Chem. Rev. 97, 449 (1997)

    CAS  Article  Google Scholar 

  9. 9.

    G.P. Ellis, in The chemistry of heterocyclic of compounds. Chromenes, Harmones and Chromones, Chapter II, ed. by A. Weissberger, E.C. Taylor (Wiley, New York, 1977), pp. 11–13

    Google Scholar 

  10. 10.

    S. Tu, B. Jiang, J. Zhang, Y. Zhang, R. Jia, C. Li, D. Zhou, L. Cao, Q. Shao. Synlett, 480 (2007)

  11. 11.

    H.A. Oskooie, M.M. Heravi, N. Karimi, M. Ebrahimzadeh, Synth. Commun. 41, 436 (2011)

    CAS  Article  Google Scholar 

  12. 12.

    A. Davoodnia, S. Allameh, S. Fazli, N. Tavakoli-Hoseini, Chem. Pap. 65, 714 (2011)

    CAS  Article  Google Scholar 

  13. 13.

    R.L. Magar, P.B. Thorat, V.B. Jadhav, S.U. Takale, S.A. Patil, R.P. Pawar, J. Mol. Catal. A Chem. 118, 374 (2013)

    Google Scholar 

  14. 14.

    A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M.M. Doroodmand, Appl. Catal. A Gen. 402, 11 (2011)

    CAS  Article  Google Scholar 

  15. 15.

    M. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A: Chem. 359, 74 (2012)

    CAS  Article  Google Scholar 

  16. 16.

    M. Abdollahi-Alibeik, F. Nezampour, Reac. Kinet. Mech. Cat. 108, 213 (2013)

    CAS  Article  Google Scholar 

  17. 17.

    G.M. Ziarani, A. Abbasi, A. Badiei, Z. Aslani, E.-J. Chem. 8, 293 (2011)

    CAS  Article  Google Scholar 

  18. 18.

    J.F. Zhou, S.J. Tu, Y. Gao, M. Ji, Chinese. J. Org. Chem. 21, 742 (2001)

    CAS  Google Scholar 

  19. 19.

    K. Rad-Moghadam, L. Yoseftabar-Miri, Tetrahedron 67, 5693 (2011)

    CAS  Article  Google Scholar 

  20. 20.

    Y. Peng, G. Song, Catal. Commun. 8, 111 (2007)

    CAS  Article  Google Scholar 

  21. 21.

    S. Zavar, Arab. J. Chem. (2012). doi:10.1016/j.arabjc.2012.07.011

    Google Scholar 

  22. 22.

    S. Banerjee, A. Horn, H. Khatri, G.R. Sereda, Tetrahedron Lett. 52, 1878 (2011)

    CAS  Article  Google Scholar 

  23. 23.

    D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagouda, R.S. Varma, Tetrahedron 63, 3093 (2007)

    CAS  Article  Google Scholar 

  24. 24.

    A. Fallah-Shojaei, K. Tabatabaeian, F. Shirini, S.Z. Hejazi, RSC Adv. (2014). doi:10.1039/C3RA46598E

    Google Scholar 

  25. 25.

    A. Alizadeh, M.M. Khodaei, M. Beygzadeh, D. Kordestani, M. Feyzi, Bull. Korean Chem. Soc. 33, 2456 (2012)

    Google Scholar 

  26. 26.

    R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal. Commun. 9, 307 (2008)

    CAS  Article  Google Scholar 

  27. 27.

    W.B. Sun, P. Zhang, J. Fan, S.H. Chen, Z.H. Zhang, Synth. Commun. 40, 587 (2010)

    CAS  Article  Google Scholar 

  28. 28.

    S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37, 1097 (2007)

    CAS  Article  Google Scholar 

  29. 29.

    X.Z. Lian, Y. Huang, Y.Q. Li, W.J. Zheng, Monatsh. Chem. 139, 129 (2008)

    CAS  Article  Google Scholar 

  30. 30.

    G. Sabitha, K. Arundhathi, K. Sudhakar, B. Sastry, J. Yadav, Synth. Commun. 39, 433 (2009)

    CAS  Article  Google Scholar 

  31. 31.

    D. Pore, K. Undale, B. Dongare, U. Desai, Catal. Lett. 132, 104 (2009)

    CAS  Article  Google Scholar 

  32. 32.

    P. Veerakumar, Z. Lu, M. Velayudham, K. Lu, S. Rajagopal, J. Mol. Catal. A 332, 128 (2010)

    CAS  Article  Google Scholar 

  33. 33.

    H. Vaidyanathan, M.W. Earl, US Patent 5654113

  34. 34.

    G. Chehardoli, M.A. Zolfigol, S.B. Azimi, E. Alizadeh, Chin. Chem. Lett. 22, 827 (2011)

    CAS  Article  Google Scholar 

  35. 35.

    N. Soltani, E. Saion, M.Z. Hussein, M. Erfani, K. Rezaee, G. Bahmanrokh, J. Inorg. Organom. Poly. 22, 830 (2012)

    CAS  Article  Google Scholar 

  36. 36.

    S. Khaksar, M. Tajbakhsh, M. Gholami, C. R. Chim. 17, 30 (2014)

    CAS  Article  Google Scholar 

  37. 37.

    S. Khaksar, M. Tajbakhsh, M. Gholami, F. Rostamnezhad, Chin. Chem. Lett. (2014). doi:10.1016/j.cclet.2014.04.008

    Google Scholar 

  38. 38.

    S. Vahdat, S. Khaksar, Res. Chem. Intermed (2014). doi:10.1007/s11164-013-1521-5

    Google Scholar 

  39. 39.

    F. Shirini, P. Najafi Moghadam, S. Moayedi, M. Seddighi, RSC Adv. 4, 38581 (2014)

    CAS  Article  Google Scholar 

  40. 40.

    X. Li, X. Wang, D. Yu, S. Ye, Q. Kuang, Q. Yi and X. Yao, J. Nanomater, 1 (2012).

  41. 41.

    N. Montazeri, T. Noghani, M. Ghorchibeigy, R. Zoghi, J. Chem. doi:10.1155/2014/596171

  42. 42.

    M.G. Dekamin, M. Eslami, A. Maleki, Tetrahedron. 69, 1074 (2013)

    CAS  Article  Google Scholar 

  43. 43.

    D.M. Pore, K.A. Undale, B.B. Dongare, U.V. Desai, Catal. Lett. 132, 104 (2009)

    CAS  Article  Google Scholar 

  44. 44.

    J. Davarpanah, A.R. Kiasat, S. Noorizadeh, M. Ghahremani, J. Mol. Catal. A 376, 78 (2013)

    CAS  Article  Google Scholar 

  45. 45.

    K. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Chin. Catal. 34, 2245 (2013)

    CAS  Article  Google Scholar 

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Acknowledgments

The authors are Grateful to the Research Council of the University of Guilan for partial support of this study.

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Correspondence to Farhad Shirini.

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Shirini, F., Abedini, M., Zarrabzadeh, S. et al. Efficient synthesis of 4H-pyran derivatives using a polymeric catalyst based on PVP. J IRAN CHEM SOC 12, 2105–2113 (2015). https://doi.org/10.1007/s13738-015-0687-8

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Keywords

  • Poly(vinylpyrrolidone)
  • Poly(vinylpyrrolidonium) hydrogen sulfate ([PVPH]HSO4)
  • 2-Amino-4H-pyran derivatives
  • Multi-component reactions