Document Type : Original Research Article

Authors

Department of Chemistry, College of Basic Science, University of Mohaghegh Ardabili 56199-11367, Ardabil, Iran

Abstract

A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. These features make this method an attractive alternative to existing routes for deprotection of imines
A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. These features make this method an attractive alternative to existing routes for deprotection of imines

Graphical Abstract

A Facile and environmental friendly method for C=N bond cleavage of imines using p-toluenesulfonic acid in solid State

Keywords

Main Subjects

[1] P.G.M. Wuts, T.W. Greene, Green′s Protective Groups in Organic Synthesis, 4rd ed.; Wiley & Sons: New York, 2007.
[2] P.J. Kocienski, Protecting Groups, Thieme: Stuttgart, 1994.
[3] R.O.C. Norman, Principle of Organic Synthesis. Chapman and Hall: London, 1978.
[4] D.J.A. Schedler, A.G. Godfrey, B. Ganem, Tetrahedron Lett., 1993, 34, 5035-5038.
[5] S.D. Sharma, P. Gogoi, M. Boruah, D. Konwar, Synth. Commun., 2007, 37, 2473-2481.
[6] G. Rao, M. Philipp, J. Org. Chem., 1991, 56, 1505-1512.
[7] J.C. Sheehan, V.J. Grenda, J. Am. Chem. Soc., 1962, 84, 2417-2420.
[8] J.N. Williams Jr, R.M. Jacobs, Biochem. Biophys. Res. Commun., 1966, 22, 695-699.
[9] A.R. Khomutov, A.S. Shvetsov, J.J. Vepsäläinen, A.M. Kritzyn, Tetrahedron Lett., 2001, 42, 2887-2889.
[10] C.G. Rao, A.S. Radhakrishna, B.B. Singh, S.P. Bhatnager, Synthesis, 1983, 808-808.
[11] J.R. Maloney, R.E. Lyle, J.E. Saavedra, G.G. Lyle, 1978, 212-213.
[12] R. Polt, L. Szabo, J. Treiberg, Y. Li, V.J. Hruby, J. Am. Chem. Soc., 1992, 114, 10249-10258.
[13] H. Alper, S. Amaratunga, J. Org. Chem., 1982, 47, 3593-3595.
[14] P. Gogoi, P. Hazarika, D. Konwar, J. Org. Chem., 2005, 70, 1934-1936.
[15] M. Ghiaci, G.H. Imanzadeh, , Synth. Commun., 1998, 28, 2275-2280.
[16] G.H. Imanzadeh, A.R. Hajipour, S.E Mallakpour, Synth. Commun., 2003, 33, 735-740.
[17] G.H. Imanzadeh, M.R. Zamanloo, H. Eskandari, K. Shayesteh, J. Chem. Res., 2006, 151-153.
[18] G.H. Imanzadeh, A.R Mosavi Zare, A. Zare, A. Khalafinezhad, A. Hasaninezhad, A. Parhami, J. Iran. Chem. Soc., 2007, 4, 467-475.
[19] G.H. Imanzadeh, F. Ahmadi, M. Zamanloo, Y. Mansoori, Molecules., 2010, 15, 7353-7362.
[20] G.H. Imanzadeh, F. Kazemi, M. Zamanloo, Y. Mansoori, Ultrason Sonochem., 2013, 20, 722-728.
[21] Dictionary of organic compounds; Chapman and Hall: London, 1996.
[22] B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, Molecules., 2002, 7, 751-755.
[23] I.O. Donkor, A. Gangiee, R.L. Kisliuk, Y. Gaumont, J. Heterocycl. Chem., 1991, 28, 1651-1655.
[24] A. Vogel, Vogel,s Practical Organic Chemistry, 4th ed.; Longman Press: London, 1978.