An efficient one-pot synthesis of α-amino nitriles using ecofriendly Lewis-acidic ionic liquid choline chloride.2ZnCl2

Iranian Journal of Catalysis

مقاله 1، دوره 2، شماره 4، اسفند 2012، صفحه 147-151   

نویسندگان

Abdol R. Hajipour^{* 1}؛ Ifa Mahboobi Dehbane²

¹Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran. Department of Pharmacology, University of Wisconsin, Medical School, 1300 University Avenue, Madison, 53706-1532, WI, USA.

²Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran.

چکیده

α-Amino nitriles are synthesized in a one-pot, three-component coupling of aldehydes (or ketones), aniline, and trimethylsilyl cyanide using a catalytic amount of choline chloride.2ZnCl2 as a bio Lewis acidic ionic liquid. Mild Lewis acidic characteristic of this ionic liquid allows efficient synthesis of α-amino nitriles from acid sensitive aldehydes.

کلیدواژه‌ها

Strecker reaction؛ α-Amino nitriles؛ Trimethylsilylcyanide؛ Choline chloride

مراجع

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

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

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

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

[5] K. Sarendra, N.S. Krishnaveni, A. Mahesh and K.R. Rao, J. Org. Chem. 71 (2006) 2532-2534.

[6] Y. Fukuda, Y. Maeda, K. Kondo and T. Aoyama, Synthesis (2006) 1937-1939.

[7] M.L. Kantam, K. Mahendar, B. Sreedhar, B.M. Choudary, Tetrahedron 64 (2008) 3351-3360.

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

[9] S. Kobayashi, H. Ishitani, Chem. Rev. 99 (1999) 1069-1094.

[10] S. Nakamura, N. Sato, M. Sugimoto and T. Toru, Tetrahedron: Asymmetr. 15 (2004) 1513-1516.

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

[12] K. Mai, G. Patil, Tetrahedron Lett. 25 (1984) 4583-4586.

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

[14] A. Heydari, P. Fatemi, A.A. Alizadeh, Tetrahedron Lett. 39 (1998) 3049-3050.

[15] S. Kobayashi, S. Nagayama and T. Busujima, Tetrahedron Lett. 37 (1996) 9221-9224.

[16] S.K. De, R.A. Gibbs, J. Mol. Catal. A: Chem. 232 (2005) 123-125.

[17] S.K. De, J. Mol. Catal. A: Chem. 225 (2005) 169-171.

[18] M.M. Mojtahedi, M. S. Abaee, T. Alishiri, Tetrahedron Lett. 50 (2009), 2322-2325.

[19] S.K. De, Synth. Commun. 35 (2005) 653-656.

[20] J. Jarusiewicz, Y. Choe, K. S. Yoo, C.P. Park and K.W. Jung, J. Org. Chem. 74 (2009) 2873-2876.

[21] S.K. De and R.A. Gibbs, Tetrahedron Lett. 45 (2004) 7407-7408.

[22] J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah, M. Srinvias, Tetrahedron 60 (2004) 1767-1771.

[23] A. Heydari, S. Khaksar, M. Pourayoubi, A.R. Mahjoub, Tetrahedron Lett. 48 (2007) 4059-4060.

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

[25] A. Heydari, S. Khaksar, M. Tajbakhsh, Tetrahedron Lett. 49 (2008) 3527-3529.

[26] P. Anastas, J.C. Warner, Green Chemisrty: Theory and Practice, Oxford University: Oxford, 1998.

[27] A.P. Abott, G. Capper, D.L. Davies, H.L. Munro, R.K. Rasheed, V. Tambyrajah, Chem. Commun. (2001) 2010-2011.

[28] A.P. Abott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Green Chem. 4 (2002) 24-26.

[29] R.C. Morales, V. Tambyrajah, P.R. Jenkins, D.L. Davies, A.P. Abott, Chem. Commun. (2004) 158-159.

[30] A.P. Abbott, G. Capper, K.J. Mckenzie, K.S. Ryder, J. Electroanal. Chem. 599 (2007) 288-294.

[31] A.P. Abott, T.J. Bell, S. Hand, B. Stoddart, Green Chem. 7 (2005) 705-707.

[32] Z. Duan, Y. Gu, Y. Deng, Catal. Commun. 7 (2006) 651-656.

[33] S.P. Wicelinski, R.J. Gale, K.M. Pamidimukkala, R.A. Laine, Anal. Chem. 60 (1988) 2228-2232.

[34] L.A. Yanovskya, C. Shachidayatov, V.E. Kutcherav, Tetrahedron 23 (1967) 1311-1316.

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

[36] 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.

[37] Ch. Csongar, I. Muller, H. Slezak, H.J. Klebsch, G. Tomaschewski, J. Prakt. Chem. 330 (1988) 1006-1014.

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

[39] K. Mai and G. Patil, Synthetic Comm. 15 (1985) 157-164.

[40] C. Wiles, P. Watts, Eur. J. Org. Chem. 33 (2008) 5597-5613.