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South African Journal of Chemistry

versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350

S.Afr.j.chem. (Online) vol.62  Durban  2009

 

RESEARCH ARTICLE

 

KHSO4-catalyzed three-component synthesis of α-aminonitriles

 

 

Hossein A. Oskooie; Majid M. Heravi; Mojgan Ebrahimzadeh; Bita Baghernejad

Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, Iran

 

 


ABSTRACT

A simple, convenient and general method has been developed for the synthesis of α-aminonitriles by a one-pot three-component condensation of aldehydes, amines and trimethyl silyl cyanide under solvent-free conditions in the presence of a catalytic amount of KHSO4 in good yields. The new method compares well in terms of yields with alternative methods. In general the reaction times are much shorter and the work up much easier.

Keywords: One-pot, KHSO4, trimethyl silyl cyanide, α-aminonitriles


 

 

Full text available only in PDF format.

 

Acknowledgements

We are thankful to Azzahra University Research Council for partial financial support.

 

References

1 Y.M. Shafran, V.A. Bakulev and VS. Mokrushin, Russ. Chem. Rev., 1989, 58, 148-162.         [ Links ]

2 L.M. Weinstock, P. Davis, B. Handelsman and R. Tull, J. Org. Chem., 1967, 32, 2823-2829.         [ Links ]

3 D. Enders and P. Shilvock, Chem. Soc. Rev., 2000, 29, 359-373.         [ Links ]

4 L. Yet, Angew. Chem., Int. Ed. Engl., 2001, 40, 875-877 and references cited therein.         [ Links ]

5 S. Harusawa, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1979, 20, 4663-4666.         [ Links ]

6 T.K. Chakraborty, G.V. Reddy and K.A. Hussain, Tetrahedron Lett., 1991, 32, 7597-7600.         [ Links ]

7 G.K.S. Prakash, T. Mathew, C. Panja, S. Alconcel, H. Vaghoo, C. Do and G.A. Olah, Proc. Natl. Acad. Sci. U.S.A., 2007, 104, 3703-3706.         [ Links ]

8 E. Takahashi, H. Fujisawa, T. Yanai and T. Mukaiyama, Chem. Lett., 2005, 34, 318-319.         [ Links ]

9 C.A. Krueger, K.W. Kuntz, C.D. Dzierba, W.G. Wirschun, J.D. Gleason, M.L. Snapper and A.H. Hoveyda, J. Am. Chem. Soc, 1999, 121, 4284-4285.         [ Links ]

10 (a) M.S. Iyer, K.M. Gigstad, N.D. Namdev and M. Lipton, J. Am. Chem. Soc., 1996, 118, 4910-911;         [ Links ] (b) E.L. Corey and M. Grogan, Org. Lett., 1999, 1, 157-159;         [ Links ] (c) M.S. Sigman, P. Vachal and E.N. Jacobsen, Angew. Chem., Int. Ed. Engl., 2000, 39, 1279-1281;         [ Links ] (d) M.S. Sigman and E.N. Jacobsen, J. Am. Chem. Soc., 1998, 120, 4901-4902;         [ Links ] (e) B. Liu, X. Feng, F. Chen, G. Zhang, X. Cui and Y. Jiang, Synlett, 2001, 1551-1553.         [ Links ]

11 J.S. Yadav, B.VS. Reddy, B. Eshwaraiah, M. Srinivas and P. Vishnu-murthy, New J. Chem., 2003, 27, 462-465.         [ Links ]

12 B.C. Ranu, S.S. Dey and A. Hajra, Tetrahedron, 2002, 58, 2529;         [ Links ] (b) S.K. De and R.A. Gibbs, Tetrahedron Lett., 2004, 45, 7407-7408.         [ Links ]

13 F.F. Bamoharram, M.M. Heravi, M. Roshani, A. Gharib and M. Jahangir, Applied Catal., 2006, 302, 42-46;         [ Links ] (b) M.M. Heravi, R. Hekmatshoar and L. Pedram, J. Mol. Catal. A: Chem., 2005, 89, 231-233;         [ Links ] (c) M. Tajbakhsh, B. Mohajerani, M.M. Heravi and A.N. Ahmadi, J. Mol. Catal. A: Chem., 2005, 236, 216-219;         [ Links ] (d) M.M. Heravi, R. Motamedi, N. SiefiandF.F. Bamoharram, J. Mol. Catal., 2006, 249, 1-3;         [ Links ] (e) M.M. Heravi, H.A. Oskooie and B. Baghernejad, J. Chin. Chem. Soc., 2007, 54, 767-770.         [ Links ]

14 Z.H. Zhang, L. Yin, Y. Li and Y.M. Wang, Tetrahedron Lett., 2005, 46, 889-893.         [ Links ]

15 G.P. Romanelli, D.Bennardi, D.M. Ruiz, G. Baronetti, H.J. Thomas and J.C. Autino, Tetrahedron Lett., 2004, 45, 8935-8939;         [ Links ] (b) I. Saxena, D.C. Borah and J.C. Sarma, Tetrahedron Lett., 2005, 46, 1159-1160;         [ Links ] (c) K.C.K. Swamy, S. Kumaraswamy, K.S. Kumar and C. Muthiah, Tetrahedron Lett., 2005, 46, 3347-3350.         [ Links ]

16 B.R. Travis, M. Sivakumar, G.O. Hollist and B. Borhan, Org. Lett, 2003, 5, 1031-1034.         [ Links ]

17 M.M. Heravi, K. Bakhtiari, S. Taheri and H.A. Oskooie, Green Chem., 2005, 7, 867-869.         [ Links ]

18 B.A.B. Prasad, A. Bisai and V.K. Singh, Tetrahedron Lett., 2004, 45, 9565-9567.         [ Links ]

19 M. Narasimhulu, T.S. Reddy, K.C. Mahesh, S.M. Reddy, A.V. Reddy and Y. Venkateswarlu, J. Mol. Catal. A: Chem, 2007, 264, 288-292.         [ Links ]

20 L. Royer, S.K. De and R.A. Gibbs, TetrahedronLett., 2005, 46, 4595-4596.         [ Links ]

21 J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah and M. Srinivas, Tetrahedron, 2004, 60, 1767-1769.         [ Links ]

22 B.C. Ranu, S.S. Dey and A. Hajra, Tetrahedron, 2002, 58, 2529-2531.         [ Links ]

23 S.K. De, Synth. Commun, 2005, 35, 653-655.         [ Links ]

24 K. Heydari, A. Arefi, S. Khaksar and R.K. Shiroodi, J. Mol. Catal. A: Chem., 2007, 271, 142-144.         [ Links ]

25 A. Shaabani and A. Maleki, Appl. Catal, 2007, 331, 149-151.         [ Links ]

 

 

Received 17 December 2008
Revised 25 February 2009
Accepted 18 March 2009

 

 

* To whom correspondence should be addressed.
E-mail: mmh1331@yahoo.com

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