Brønsted acidic ionic liquid as a metal free catalyst for the one-pot synthesis of α-aminonitriles under mild and solvent-free conditions

Authors

1 Department of Science, Khorasgan Branch, Islamic Azad University, Isfahan 81595-158, Iran.

2 Department of Science, Fasa Branch, Islamic Azad University, Post Box No 364, Fasa, 7461713591, Fars, Iran.

3 Dept. of Pharmacology, University of Wisconsin, Medical School, Madison, 53706-1532, WI, USA. Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, IR Iran.

4 Department of Science, Najafabad Branch, Islamic Azad University, Isfahan, Iran.

Abstract

An efficient, mild and environmentally friendly method was developed for the Strecker reaction to synthesize α-aminonitriles in the presence of methyl imidazolium hydrogen sulfate ([Hmim][HSO4]) as an efficient catalyst. These syntheses were performed via a one-pot three-component condensation of aldehydes (or ketones), amines, and trimethylsilyl cyanide under mild and solvent free conditions.

Keywords


[1] A. Strecker, Ann. Chem. Pharm. 75 (1850) 27-45.

[2] Y.M. Shafran, V.A. Bakulev, V.S. Mokrushin, Russ. Chem. Rev. 58 (1989) 148-162.

[3] X. Huang, J. Huang, Y. Wen, X. Feng, Adv. Synth. Catal., 348 (2006) 2579-2584.

[4] T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 347 (2005) 1523-1528.

[5] J. March, Advanced Organic Chemistry, 4th ed.; John Wiley: New York, (1999) 965-966.

[6] G. Dyker, Angew. Chem. Int. Ed. 36 (1997) 1700-1702.

[7] J. A. Gonzailez-Vera, M. T. Garcia-Lopez, R. Herranz, J. Org. Chem. 70 (2005) 3660-3666.

[8] D. Enders, J.P. Shilvock, Chem. Soc. Rev. 29 (2000) 359-373.

[9] L. M. Weinstock, P. Davis, B. Handelsman, R. A. Tull, J. Org. Chem. 32 (1967) 2823-2829.

[10] 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) 901-908.

[11] R.O. Duthaler, Tetrahedron 50 (1994) 1539-1650.

[12] B.A. Bhanu Prasad, A. Bisai, V.K. Singh, Tetrahedron Lett. 45 (2004) 9565-9567.

[13] S. Nakamura, N. Sato, M. Sugimoto, T. Toru, Tetrahedron Asymmetry 15 (2004) 1513-1516.

[14] S. Harusawa, Y. Hamada, T. Shioiri, Tetrahedron Lett. 20 (1979) 4663-4666.

[15] P. Vachal, E.N. Jacobsen, J. Am. Chem. Soc. 124 (2002) 10012-10014.

[16] A. Heydari, S. Khaksar, M. Tajbakhsh, Tetrahedron Lett. 50 (2009) 77-80.

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

[18] N.H. Khan, S. Agrawal, R.I. Kureshy, S.H.R. Abdi, S. Singh, E. Suresh, R. V. Jasra, Tetrahedron Lett. 49 (2008) 640-644.

[19] S. Paraskar, A. Sudalai, Tetrahedron Lett. 47 (2006) 5759-5762.

[20] A. Shaabani, A. Maleki, Appl. Catal A: Genl 331 (2007) 149-151.

[21] B. Karmakar, J. Banerji, Tetrahedron Lett. 51 (2010) 2748-2750.

[22] B.M. Reddy, B. Thirupathi, M.K. Patil, J. Mol. Catal. A: Chem. 307 (2009) 154-159.

[23] H.A. Arefi, S. Khaksar, R.K. Shiroodi, J. Mol. Catal. A: Chem. 271 (2007) 142-144.

[24] B.C. Ranu, S.S. Dey, A. Hajra, Tetrahedron 58 (2002) 2529-2532.

[25] S.M. Vahdat, S. Khaksar, M. Khavarpour, Chin. Chem. Lett. 22 (2011) 543-546.

[26] K. Niknam, D. Saberi, M. NouriSefat, Tetrahedron Lett. 51 (2010) 2959-2962.

[27] S.M. Baghbanian, M. Farhang, R. Baharfar, Chin. Chem. Lett. 22 (2011) 555-558.

[28] A.R. Hajipour, Y. Ghayeb, N. Sheikhan, J. Iran. Chem. Soc. 7 (2010) 447-454.

[29] B. Karmakar, A. Sinhamahapatra, A.B. Panda, J. Banerji, B. Chowdhury, Appl. Catalysis A: General, 392 (2011) 111-117.

[30] a) T. Welton, Chem. Rev. 99 (1999) 2071-2083. b) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772-3789.

[31] T.L. Greaves, C.J. Drummond, Chem. Rev. 108 (2008) 206-237.

[32] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Catal. Commun. 9 (2008) 89-96.

[33] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, J. Sulfur Chem. 30 (2009) 46-52.

[34] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Phosphorus Sulfur 184 (2009) 705-711.

[35] D. Zhao, Y. Liao, Z. Zhang, Clean 35 (2007) 42-48.

[36] R. Martinez, D.J. Ramon, M. Yus, Tetrahedron Lett. 46 (2005) 8471-8474.