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New application of decaniobate salt as basic solid in the synthesis of 4H-pyrans by microwave assisted multicomponent reactions

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Abstract

This study focuses on the search of new applications of polyoxometalates known as decaniobate ions [Nb10O28]6−. The decaniobates can be used as basic solid catalysts in multicomponent reactions to obtain good yields to 4H-pyrans (> 95%) under microwave radiation and solvent-free conditions, using several aldehydes with different electron-withdrawing or electron donor substituents. The synthesis of (TMA)6 [Nb10O28]6H2O was performed following a simple protocol (HPNb), which was modified to decrease the number of hexaniobate species that are formed as impurities (HPNb-HF).

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References

  1. C.A. Ohlin, E.M. Villa, W.H. Casey, Inorg. Chim. Acta. 362, 1391 (2009)

    Article  CAS  Google Scholar 

  2. Y. Ye, C. Chen, H. Feng, J. Zhou, J. Ma, J. Chen, Open J. Inorg. Chem. 3, 59 (2013)

    CAS  Google Scholar 

  3. L. Shen, Y.-Q. Xu, Y.-Z. Gao, F.-Y. Cui, C.-W. Hu, J. Mol. Struct. 934, 37 (2009)

    Article  CAS  Google Scholar 

  4. P. Huang, C. Qin, Z.-M. Su, Y. Xing, X.-L. Wang, K.-Z. Shao, J. Am. Chem. Soc. 134, 14004 (2012)

    Article  CAS  PubMed  Google Scholar 

  5. M. Nyman, Dalton Trans. 40, 8049 (2011)

    Article  CAS  PubMed  Google Scholar 

  6. S. Hayashi, S. Yamazoe, K. Koyasu, T. Tsukuda, RSC Adv. 6, 16239 (2016)

    Article  CAS  Google Scholar 

  7. S. Hayashi, S. Yamazoe, K. Koyasu, T. Tsukuda, Chem. An Asian J. 12, 1635 (2017)

    Article  CAS  Google Scholar 

  8. R. Pagadala, S. Maddila, S. Jonnalagadda, J. Heterocycl. Chem. 52, 1226 (2015)

    Article  CAS  Google Scholar 

  9. H. Valizadeh, A. Azimi, J. Iran. Chem. Soc. 8, 123 (2011)

    Article  CAS  Google Scholar 

  10. R.M.N. Kalla, M.R. Kim, I. Kim, Tetrahedron Lett. 56, 717 (2015)

    Article  CAS  Google Scholar 

  11. G.P. Lu, C. Cai, J. Heterocycl. Chem. 48, 124 (2011)

    Article  CAS  Google Scholar 

  12. S. Balalaie, S. Ramezanpour, M. Bararjanian, J.H. Gross, Catal. Commun. 38, 1078 (2008)

    CAS  Google Scholar 

  13. S. Sadjadi, M.M. Heravi, V. Zadsirjan, V. Farzaneh, Appl. Surf. Sci. 426, 881 (2017)

    Article  CAS  Google Scholar 

  14. E. Nope, J.J. Martínez, H.A. Rojas, Á.G. Sathicq, G.P. Romanelli, Res. Chem. Intermed. 43, 2103 (2017)

    Article  CAS  Google Scholar 

  15. E. Ruijter, R. Scheffelaar, R.V. Orru, Angew Chem. Int. Ed. 50, 6234 (2011)

    Article  CAS  Google Scholar 

  16. L.M. Sanchez, H.J. Thomas, G.P. Romanelli, Mini Rev. Org. Chem. 12, 115 (2015)

    Article  CAS  Google Scholar 

  17. N.R. Guha, D. Bhattacherjee, P. Das, Tetrahedron Lett. 55, 2912 (2014)

    Article  CAS  Google Scholar 

  18. E.D.J.M. Prieto, B. Rivas, J. Sánchez, Cienc en Desarro. 4, 219 (2013)

    Google Scholar 

  19. K. Badamali, R. Luque, J.H. Clark, S.W. Breeden, Catal. Commun. 10, 1010 (2009)

    Article  CAS  Google Scholar 

  20. R. Das, J. Ray, P. Pramanik, J. Mater. Res. 15, 2273 (2000)

    Article  CAS  Google Scholar 

  21. K. Tanabe, T. Yamaguchi, J. Res. Inst. Catal. Hokkaido Univ. 11, 179 (1964)

    CAS  Google Scholar 

  22. P. Chagas, H.S. Oliveira, R. Mambrini, M. Le Hyaric, M.V. de Almeida, L.C. Oliveira, Appl. Catal. A Gen. 454, 88 (2013)

    Article  CAS  Google Scholar 

  23. M. Aureliano, C.A. Ohlin, M.O. Vieira, M.P. Marques, W.H. Casey, L.A. de Carvalho, Dalton Trans. 45, 7391 (2016)

    Article  CAS  PubMed  Google Scholar 

  24. A.L. Shiguihara, M.A. Bizeto, V.R. Constantino, J. Braz. Chem Soc. 21, 1366 (2010)

    Article  CAS  Google Scholar 

  25. E.J. Graeber, B. Morosin, Acta Crystallogr. Sect B. 33, 2137 (1977)

    Article  Google Scholar 

  26. J.-H. Son, C.A. Ohlin, W.H. Casey, Dalton Trans. 42, 7529 (2013)

    Article  CAS  PubMed  Google Scholar 

  27. A. Fielicke, G. Meijer, G. Helden, J. Am. Chem. Soc. 125, 3659 (2003)

    Article  CAS  PubMed  Google Scholar 

  28. J. Niu, X. Fu, J. Zhao, S. Li, P. Ma, J. Wang, Cryst. Growth Des. 10, 3110 (2010)

    Article  CAS  Google Scholar 

  29. S.W. Kshirsagar, N.R. Patil, S.D. Samant, Synth. Commun. 41, 1320 (2011)

    Article  CAS  Google Scholar 

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Acknowledgements

We thank COLCIENCIAS for the financial support under Project No. 110965843004. EN, GPR and AGS thank to UNLP, CONICET, MYNCIT and ERANET-1.

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Correspondence to Gustavo P. Romanelli or José J. Martínez.

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Gutierrez, L.F., Nope, E., Rojas, H.A. et al. New application of decaniobate salt as basic solid in the synthesis of 4H-pyrans by microwave assisted multicomponent reactions. Res Chem Intermed 44, 5559–5568 (2018). https://doi.org/10.1007/s11164-018-3440-y

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