Skip to main content
SpringerLink
Log in

[Bmim]5[PNiW11O39]·3H2O an organic–inorganic hybrid as catalyst for one-pot pseudo-five-component synthesis of tetrazolyldiazepines

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

In this research, two heterogeneous organic–inorganic hybrid catalysts, [bmim]3[PW12O40]·3H2O and [bmim]5[PNiW11O39]·3H2O, have been prepared. The catalysts were fully characterized by several techniques such as elemental analyses, Fourier transform infrared spectroscopy, thermo-gravimetric analysis, scanning electron microscope and energy-dispersive X-ray analysis. Next, the hybrid catalysts have been used for the synthesis of functionalized diazepines containing tetrazole ring. Tetrazolyl-1H-spiro[benzo[b]cyclopenta[e][1,4] diazepines products were obtained in excellent yields and mild experimental conditions using [bmim]5[PNiW11O39]·3H2O as catalyst. This process was carried out via a one-pot, pseudo-five-component condensation reaction by means of a 1,2-diamine, isocyanide, TMSN3 and two molecules of a linear or cyclic ketone in methanol, at ambient temperature.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 3
Fig. 5
Fig. 6
Scheme 4
Scheme 5

Similar content being viewed by others

References

  1. R.A. Sheldon, I. Arends, U. Hanefeld, Green Chemistry and Catalysis (Wiley–VCH, Weinheim, 2007)

    Book  Google Scholar 

  2. R.P. Herrera, E. Marqués-LÃpez, Multicomponent Reactions: Concepts and Applications for Design and Synthesis (Wiley, Hoboken, 2015)

    Book  Google Scholar 

  3. J. Zhu, H. Bienayme, Multicomponent Reactions (Wiley–VCH, Weinheim, 2005)

    Book  Google Scholar 

  4. A. Dömling, Chem. Rev. 106, 17–89 (2006)

    Article  Google Scholar 

  5. V. Nenajdenko, Isocyanide Chemistry: Applications in Synthesis and Material Science (Wiley–VCH, Weinheim, 2012)

    Book  Google Scholar 

  6. N. Elders, E. Ruijter, F.J.J. de Kanter, M.B. Groen, R.V.A. Orru, Chem. Eur. J. 14, 4961–4973 (2008)

    Article  CAS  Google Scholar 

  7. E. Rafiee, F. Mirnezami, J. Mol. Liq. 199, 156–161 (2014)

    Article  CAS  Google Scholar 

  8. A. Hamiov, H. Cohen, R. Neumann, J. Am. Chem. Soc. 126, 11762–11763 (2004)

    Article  Google Scholar 

  9. J.R.H. Ross, Heterogeneous Catalysis: Fundamentals and Applications, 1st edn. (Elsevier, Amsterdam, 2012)

    Google Scholar 

  10. A.P. Wight, M.E. Davis, Chem. Rev. 102, 3589–3614 (2002)

    Article  CAS  Google Scholar 

  11. M. Mizuno, M. Takahashi, Y. Tokuda, T. Yoko, Chem. Mater. 18, 2075–2084 (2006)

    Article  CAS  Google Scholar 

  12. J.A. Joule, K. Mills, Heterocyclic Chemistry, 4th edn. (Blackwell, Hoboken, 2000)

    Google Scholar 

  13. C. Valdes, M. Bayod, Modern Heterocyclic Chemistry: The chemistry of Benzodiazepines, ed. by J. Alvarez-Builla, J.J. Vaquero, J. Barluenga, chap 25, (Wiley–VCH, 2012), pp. 2175–2229

  14. F.R. Benson, Chem. Rev. 41, 1–61 (1947)

    Article  CAS  Google Scholar 

  15. G.I. Koldobskii, V.A. Ostrovskii, V.S. Popavskii, Chem. Heterocycl. Comp. 17, 965–988 (1981)

    Article  Google Scholar 

  16. V.J. Merluzzi, K.D. Hargrave, M. Labadia, K. Grozinger, M. Skoog, J.C. Wu, C.K. Shih, K. Eckner, S. Hattox, J. Adams, A.S. Rosenthal, R. Faanes, R.J. Eckner, R.A. Koup, J.L. Sullivan, Science 250, 1411–1413 (1990)

    Article  CAS  Google Scholar 

  17. D. Sasayama, H. Hori, T. Teraishi, K. Hattori, M. Ota, J. Matsuo, Y. Kinoshita, M. Okazaki, K. Arima, N. Amano, T. Higuchi, H. Kunugi, J. Psychiatr. Res. 49, 37–42 (2014)

    Article  Google Scholar 

  18. W. Werner, J. Baumgart, G. Burckhardt, W.F. Fleck, K. Geller, W. Gutsche, H. Hanschmann, A. Messerschmidt, W. Roemer, Biophys. Chem. 35, 271–285 (1990)

    Article  CAS  Google Scholar 

  19. A.J. Zych, R.J. Herr, Pharma. Chem. 6, 21–24 (2007)

    CAS  Google Scholar 

  20. S.-X. Wanga, Z. Fang, Z.-J. Fan, D. Wang, Y.-D. Li, X.-T. Ji, X.-W. Hua, Y. Huang, T.A. Kalinina, V.A. Bakulev, Y.Y. Morzherin, Chin. Chem. Lett. 24, 889–892 (2013)

    Article  Google Scholar 

  21. M.A. Malik, S.A. al-Thabaiti, Int. J. Mol. Sci. 13, 10880–10898 (2012)

    Article  CAS  Google Scholar 

  22. I. Ueda, K. Ishii, K. Sinozaki, M. Seiki, M. Hatanaka, Chem. Pharm. Bull. 39, 1430–1435 (1991)

    Article  CAS  Google Scholar 

  23. W.H. Song, M.M. Liu, D.W. Zhong, Y.L. Zhu, M. Bosscher, L. Zhou, D.Y. Ye, Z.H. Yuan, Bioorg. Med. Chem. Lett. 23, 4528–4531 (2013)

    Article  CAS  Google Scholar 

  24. Y. Shen, J. Han, X. Sun, X. Wang, J. Chen, H. Deng, M. Shao, H. Shi, H. Zhang, W. Cao, Tetrahedron 71, 4053–4060 (2015)

    Article  CAS  Google Scholar 

  25. Z. Noroozi-Tisseh, M. Dabiri, M. Nobahar, H.R. Khavasi, A. Bazgir, Tetrahedron 68, 1769–1773 (2012)

    Article  Google Scholar 

  26. A. Shaabani, A.H. Rezayan, S. Keshipour, A. Sarvary, S.W. Ng, Org. Lett. 11, 3342–3345 (2009)

    Article  CAS  Google Scholar 

  27. H. Rodríguez, M. Suárez, F. Albericio, Molecules 17, 7612–7628 (2012)

    Article  Google Scholar 

  28. A.H. Kategaonkar, V.B. Labada, P.V. Shinda, A.H. Kategaonkar, B.B. Shingate, M.S. Shingare, Monatsh. Chem. 141, 787–791 (2010)

    Article  CAS  Google Scholar 

  29. R.S. Borisov, A.I. Polyakov, L.A. Medvedeva, V.N. Khrustalev, N.I. Guranova, L.G. Voskressensky, Org. Lett. 12, 1609–1615 (2010)

    Article  Google Scholar 

  30. R.S. Borisov, A.I. Polyakov, L.A. Medvedeva, N.I. Guranova, L.G. Voskressensky, Russ. Chem. Bull. Int. Ed. 61, 3894–3897 (2012)

    Google Scholar 

  31. A. Shaabani, H. Mofakham, S. Mousavifaraz, Synlett. 731–736 (2012)

  32. H. Mofakham, A. Shaabani, S. Mousavifaraz, F. Hajishaabanha, S. Shaabani, S.W. Ng, Mol. Divers. 16, 351–356 (2012)

    Article  CAS  Google Scholar 

  33. S. Gunawan, M. Ayaz, F.D. Moliner, B. Frett, C. Kaiser, N. Patrick, Z. Xu, C. Hulme, Tetrahedron 68, 5606–5611 (2012)

    Article  CAS  Google Scholar 

  34. S.G. Yerande, K.M. Newase, B. Singh, A. Boltjes, A. Dömling, Tetrahedron Lett. 55, 3263–3266 (2014)

    Article  CAS  Google Scholar 

  35. L. Kosychova, R. Vidziunaite, G. Mikulskiene, I. Bratkovskaja, R. Jancienea, ARKIVOC 71, 87 (2015)

    Google Scholar 

  36. A. Rahmati, A. Moazzam, Z. Khalesi, Tetrahedron Lett. 70, 3840–3843 (2014)

    Article  Google Scholar 

  37. A. Rahmati, S. Ahmadi, M. Ahmadi-Varzaneh, Tetrahedron 70, 9512–9521 (2014)

    Article  CAS  Google Scholar 

  38. L. Yang, Y. Qi, X. Yuan, J. Shen, J. Kim, J. Mol. Catal. A Chem. 229, 199–205 (2005)

    Article  CAS  Google Scholar 

  39. Y. Chen, J. Zhuang, X. Liu, J. Gao, X. Han, X. Bao, N. Zhou, S. Gao, Z. Xi, Catal. Lett. 93, 41–46 (2004)

    Article  CAS  Google Scholar 

  40. T.D. Le, K.D. Nguyen, V.T. Nguyen, T. Truong, N.T.S. Phan, J. Catal. 333, 94–101 (2016)

    Article  CAS  Google Scholar 

  41. A. Shaabani, A. Maleki, H. Mofakham, J. Comb. Chem. 10, 595–598 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

We gratefully acknowledge financial support from the Research Council of the University of Isfahan.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Isfahan, P. O. Box 81746-73441, Isfahan, Iran

    Sajad Mousavifaraz, Zahra Nadealian, Valiollah Mirkhani & Abbas Rahmati

Authors
  1. Sajad Mousavifaraz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zahra Nadealian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Valiollah Mirkhani
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Abbas Rahmati
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abbas Rahmati.

Ethics declarations

Conflict of interest

None of the authors has any potential conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mousavifaraz, S., Nadealian, Z., Mirkhani, V. et al. [Bmim]5[PNiW11O39]·3H2O an organic–inorganic hybrid as catalyst for one-pot pseudo-five-component synthesis of tetrazolyldiazepines. J IRAN CHEM SOC 14, 1753–1763 (2017). https://doi.org/10.1007/s13738-017-1116-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-017-1116-y

Keywords

Search

Navigation