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Zr(HSO4)4 catalyzed one-pot strecker synthesis of α-amino nitriles from aldehydes and ketones under solvent-free conditions

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Abstract

A mild and efficient method has been developed for the preparation of α-amino nitriles from the condensation of aldehydes and ketones with aniline and TMSCN in the presence of a catalytic amount of Zr(HSO4)4 under solvent-free conditions at room temperature.

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References

  1. A. Strecker, Ann. Chem. Pharm. 75 (1850) 27.

    Google Scholar 

  2. Y.M. Shafran, V.A. Bakulev, V.S. Mokrushin, Russ. Chem. Rev. 58 (1989) 148.

    Google Scholar 

  3. L.M. Weinstock, P. Davis, B. Handelsman, R. Tull, J. Org. Chem. 32 (1967) 2823

    CAS  Google Scholar 

  4. W.L. Matier, D.A. Owens, W.T. Comer, D. Deitchman, H.C. Ferguson, R.J. Seidehamel, J.R. Young, J. Med. Chem. 16 (1973) 901

    CAS  Google Scholar 

  5. R.O. Duthaler, Tetrahedron 50 (1994) 1539.

    CAS  Google Scholar 

  6. D. Enders, J.P. Shilvock, Chem. Soc. Rev. 29 (2000) 359

    CAS  Google Scholar 

  7. J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1999, p. 965

    Google Scholar 

  8. G. Dyker, Angew. Chem. Int. Ed. 36 (1997) 1700

    CAS  Google Scholar 

  9. J.A. Gonzaýlez-Vera, M.T. Garcýa-Lopez, R. Herranz, J. Org. Chem. 70 (2005) 3660.

    Google Scholar 

  10. D. Enders, J.P. Shilvock, Chem. Soc. Rev. 29 (2000) 359.

    CAS  Google Scholar 

  11. S. Kobayashi, H. Ishitani, Chem. Rev. 99 (1999) 1069.

    CAS  Google Scholar 

  12. P. Vachal, E.N. Jacobsen, J. Am. Chem. Soc. 124 (2002) 10012.

    CAS  Google Scholar 

  13. S. Nakamura, N. Sato, M. Sugimoto, T. Toru, Tetrahedron: Asymmetry 15 (2004) 1513.

    CAS  Google Scholar 

  14. S. Harusawa, Y. Hamada, T. Shioiri, Tetrahedron Lett. 20 (1979) 4664.

    Google Scholar 

  15. B.A. Bhanu Prasad, A. Bisai, V.K. Singh, Tetrahedron Lett. 45 (2004) 9565.

    Google Scholar 

  16. W.C. Groutas, D. Felker, Synthesis (1980) 861.

    Google Scholar 

  17. S.K. De, J. Mol. Catal. A: Chem. 225 (2005) 169.

    CAS  Google Scholar 

  18. S. Paraskar, A. Sudalai, Tetrahedron Lett. 47 (2006) 5759.

    CAS  Google Scholar 

  19. S.K. De, Synth. Commun. 35 (2005) 653.

    CAS  Google Scholar 

  20. L. Royer, S.K. De, R.A. Gibbs, Tetrahedron Lett. 46 (2005) 4595.

    CAS  Google Scholar 

  21. M. Narasimhulu, T.S. Reddy, K.C. Mahesh, S.M. Reddy, A.V. Reddy, Y. Venkateswarlu, J. Mol. Catal. A: Chem. 264 (2007) 288.

    CAS  Google Scholar 

  22. B.C. Ranu, S.S. Dey, A. Hajra, Tetrahedron 58 (2002) 2529.

    CAS  Google Scholar 

  23. A. Majhi, S.S. Kim, S.T. Kadam, Tetrahedron 64 (2008) 5509.

    CAS  Google Scholar 

  24. N.H. Khan, S. Agrawal, R.I. Kureshy, S.H.R. Abdi, S. Singh, E. Suresh, R.V. Jasra, Tetrahedron Lett. 49 (2008) 640.

    CAS  Google Scholar 

  25. J.S. Yadav, S.B.V. Reddy, B. Eeshwaraian, M. Srinivas, Tetrahedron 60 (2004) 1767.

    CAS  Google Scholar 

  26. E. Rafiee, S. Rashidzadeh, A. Azad, J. Mol. Catal. A: Chem. 261 (2007) 49.

    CAS  Google Scholar 

  27. H.A. Arefi, S. Khaksar, R.K. Shiroodi, J. Mol. Catal. A: Chem. 271 (2007) 142.

    Google Scholar 

  28. A. Shaabani, A. Maleki, App. Catalysis A: General 331 (2007) 149.

    CAS  Google Scholar 

  29. K. Matsumoto, J.C. Kim, N. Hayashi, G. Jenner, Tetrahedron Lett. 43 (2002) 9167.

    CAS  Google Scholar 

  30. G. Jenner, R.B. Salem, J.C. Kim, K. Matsumoto, Tetrahedron Lett. 44 (2003) 447.

    CAS  Google Scholar 

  31. G.K.S. Prakash, T. Mathew, C. Panja, S. Alconcel, H. Vaghoo, C. Do, G.A. Olah, Proc. Natl. Acad. Sci. USA 104 (2007) 3703.

    CAS  Google Scholar 

  32. A.R. Hajipour, A. Zarei, L. Khazdooz, B.B.F. Mirjalili, N. Sheikhan, S. Zahmatkesh, A.E. Ruoho, Synthesis 20 (2005) 3644.

    Google Scholar 

  33. A.R. Hajipour, M. Arbabian, A.E. Ruoho, J. Org. Chem. 67 (2002) 8622; b) A.R. Hajipour, B.B.F. Mirjalili, A. Zarei, L. Khazdooz, A.E. Ruoho, Tetrahedron Lett. 45 (2004) 6607.

    CAS  Google Scholar 

  34. A.R. Hajipour, B. Kooshki, A.E. Ruoho, Tetrahedron Lett. 46 (2005) 5503.

    CAS  Google Scholar 

  35. B.B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, N. Sheikhan, J. Chin. Chem. Soc. 53 (2006) 95.

    Google Scholar 

  36. F. Shirini, M.A. Zolfigol, A. Safari, I. Mohammadpoor-Baltork, B.B.F. Mirjalili, Tetrahedron Lett. 44 (2003) 7463.

    CAS  Google Scholar 

  37. F. Shirini, M.A. Zolfigol, A. Safari, J. Chem. Res. (S) (2006) 154.

    Google Scholar 

  38. B.B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, M.A. Karimi-Zarchi, Z. Zaghaghi, M. Parvaideh, J. Iran. Chem. Soc. 4 (2007) 340.

    Article  CAS  Google Scholar 

  39. R. Martinez, D.J. Ramon, M. Yus, Tetrahedron Lett. 46 (2005) 8471.

    CAS  Google Scholar 

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Hajipour, A.R., Ghayeb, Y. & Sheikhan, N. Zr(HSO4)4 catalyzed one-pot strecker synthesis of α-amino nitriles from aldehydes and ketones under solvent-free conditions. JICS 7, 447–454 (2010). https://doi.org/10.1007/BF03246031

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  • DOI: https://doi.org/10.1007/BF03246031

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