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Application of SiO2-Pr-SO3H as an efficient catalyst in the Ritter reaction

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Abstract

Sulfonic-acid-functionalized silica was applied as an efficient heterogeneous acid catalyst in the Ritter reaction to prepare amides by reaction of various benzylic, allylic, and tertiary alcohols with various nitriles in good to excellent yields under solvent-free conditions. The simplicity of the reaction, recovery of catalyst without loss of reactivity, high yield of products, and short reaction time represent improvements over many existing methods.

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References

  1. F.R. Benson, J.J. Ritter, J. Am. Chem. Soc. 71, 4128 (1949). doi:10.1021/ja01180a075

    Article  CAS  Google Scholar 

  2. J.J. Ritter, J. Kalish, J. Am. Chem. Soc. 70, 4048 (1948). doi:10.1021/ja01192a023

    Article  CAS  Google Scholar 

  3. J.J. Ritter, P.P. Minieri, J. Am. Chem. Soc. 70, 4045 (1948). doi:10.1021/ja01192a022

    Article  CAS  Google Scholar 

  4. G.C. Gullickson, D.E. Lewis, Synthesis 5, 681 (2003). doi:10.1055/s-2003-38069

    Google Scholar 

  5. F. Tamaddon, M. Khoobi, E. Keshavarz, Tetrahedron Lett. 48, 3643 (2007). doi:10.1016/j.tetlet.2007.03.134

    Article  CAS  Google Scholar 

  6. R. Sanz, A. Martinez, V. Guilarte, J.M. Alvarez-Gutierrez, F. Rodriguez, Eur. J. Org. Chem. 2007, 4642 (2007). doi:10.1002/ejoc.200700562

    Article  Google Scholar 

  7. M. Barbero, S. Bazzi, S. Cadamuro, S. Dughera, Eur. J. Org. Chem. 2009, 430 (2009). doi:10.1002/ejoc.200800931

    Article  Google Scholar 

  8. L. Ma’mani, A. Heydari, M. Sheykhan, Appl. Catal. A Gen. 384, 122 (2010). doi:10.1016/j.apcata.2011.01.015

    Article  Google Scholar 

  9. R.G. Kalkhambkar, S.N. Waters, K.K. Laali, Tetrahedron Lett. 52, 867 (2011)

    Article  CAS  Google Scholar 

  10. J.R. Norell, J. Org. Chem. 35, 1611 (1970)

    Article  CAS  Google Scholar 

  11. B.V. Subba Reddy, N. Sivasankar Reddy, C. Madan, J.S. Yadav, Tetrahedron Lett. 51, 4827 (2010). doi:10.1016/j.tetlet.2010.07.032Document

    Article  CAS  Google Scholar 

  12. R. Vardanyan, V.J. Hruby, Synthesis of essential drugs, 1st edn. (Elsevier, Amsterdam, 2006), p. 137

    Google Scholar 

  13. J. Clayden, N. Greeves, S. Warren, P. Worthers, Organic Chemistry (Oxford University Press, New York, 2001)

    Google Scholar 

  14. L. Kürti, B. Czakó, Strategic applications of named reactions in organic synthesis: background and detailed mechanisms (Academic, Burlington, 2005)

    Google Scholar 

  15. R.V. Grieken, J.A. Melero, G. Morales, J. Mol. Catal. A: Chem. 256, 29 (2006)

    Article  Google Scholar 

  16. G.M. Ziarani, A. Badiei, M. Azizi, P. Zarabadi, Iran. J. Chem. Chem. Eng. 3, 59 (2011)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  18. G.M. Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arab. J. Chem. (2011 in press corrected proof). doi: 10.1016/j.arabjc.2011.01.037

  19. G.M. Ziarani, A.R. Badiei, M. Azizi, Sci. Iran. 18, 453 (2011). doi:10.1016/j.scient.2011.05.008

    Article  CAS  Google Scholar 

  20. G.M. Ziarani, A. Badiei, A. Abbasi, Z. Farahani, Chin. J. Chem. 27, 1537 (2009)

    Article  CAS  Google Scholar 

  21. E. Callens, A.J. Burton, A.G.M. Barrett, Tetrahedron Lett. 47, 8699 (2006). doi:10.1016/j.tetlet.2006.10.023

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge the financial support from the Research Council of Alzahra University and the University of Tehran.

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Correspondence to Ghodsi Mohammadi Ziarani.

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Mohammadi Ziarani, G., Badiei, A., Dashtianeh, Z. et al. Application of SiO2-Pr-SO3H as an efficient catalyst in the Ritter reaction. Res Chem Intermed 39, 3157–3163 (2013). https://doi.org/10.1007/s11164-012-0828-y

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  • DOI: https://doi.org/10.1007/s11164-012-0828-y

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