Sulfuric acid {[3-(3-silicapropyl)sulfanyl]propyl}ester as a recyclable solid acid catalyst for the synthesis of α-amino nitriles
الموضوعات : Iranian Journal of CatalysisSomayeh Ghasemi 1 , Mojtaba Baghernejad 2 , Khodabakhsh Niknam 3
1 - Department of Chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.
2 - Young Researchers and Elite Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.
3 - Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran.
الکلمات المفتاحية: Synthesis, Aldehydes, Catalyst, α-Amino nitriles, Sulfuric acid {[3-(3-silicapropyl)sulfanyl]propyl}ester, Amines,
ملخص المقالة :
Sulfuric acid {[3-(3-silicapropyl)sulfanyl]propyl}ester (SASPSPE) is employed as a recyclable catalyst for the synthesis of α-amino nitriles. These syntheses were performed via a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide under mild reaction conditions at room temperature. The catalyst could be recycled and reused several times without any loss of efficiency.
[1] Strecker, Ann. Chem. Pharm. 75 (1850) 27-45.
[2] J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, p. 965, 1995.
[3] L.M. Weinstock, P. Davis, B. Handelsman, R. Tull, J. Org. Chem., 32 (1967) 2823-2829.
[4] W.L. Matier, D.A. Owens, W.T. Comer, D. Dietchman, H.C. Ferguson, R.J. Seidehamel, J.R. Young, J. Med. Chem., 16 (1973) 901-908.
[5] A.A. S. El-Ahl, Synth. Commun., 33 (2003) 989-998.
[6] B.C. Ranu, S.S. Dey, S. Hajra, Tetrahedron, 58 (2002) 2529-2532.
[7] J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah, M. Srinivas, P. Vishnumurthy, New J. Chem., 27 (2003) 462-465.
[8] J.S. Yadav, B.V.S. Reddy, B. Eswaraiah, M. Srinivas, Tetrahedron, 60 (2004) 1767-1771.
[9] W.Y. Chen, J. Lu, Synlett, (2005) 2293-2296.
[10] S.H. Wang, L.F. Zhao, Z.M. Du, Chin. J. Chem., 24 (2006) 135-137.
[11] 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.
[12] A. Shaabani, A. Maleki, M.R. Soudi, H. Mofakham, Catal. Commun., 10 (2009) 945-949.
[13] B. Karimi, D. Zareyee, J. Mater. Chem., 19 (2009) 8665-8670.
[14] K. Niknam, D. Saberi, M. Nouri Sefat, Tetrahedron Lett., 51 (2010) 2959-2962.
[15] M.Z. Kassaee, H. Masrouri, F. Movahedi, Appl. Catal. A: Gen., 395 (2011) 28-33.
[16] M. Nouri Sefat, D. Saberi, K. Niknam, Catal.` Lett., 141 (2011) 1713-1720.
[17] T. Rahi, M. Baghernejad, K. Niknam, Chin. Chem. Lett., 23 (2012) 1103-1106.
[18] T. Rahi, M. Baghernejad, K. Niknam, Chin. J. Catal., 33 (2012) 1095-1100.
[19] D. Chaturvedi, A.K. Chaturvedi, N. Mishra, V. Mishra, Tetrahedron Lett., 53 (2012) 5398-5401.
[20] A.R. Hajipour, I.M. Dehbane, Iran. J. Catal., 2 (2012) 147-151.
[21] A. Nasreen, Tetrahedron Lett., 54 (2013) 3797-3800.
[22] J. Leblanc, H.W. Gibson, Tetrahedron Lett., 33 (1992) 6295-6298.
[23] A. Heydari, P. Fatemi, A.A. Alizadeh, Tetrahedron Lett., 39 (1998) 3049-3050.
[24] B. Das, R. Ramu, B. Ravikanth, K.R. Reddy, Synthesis (2006) 1419-1422.
[25] K. Niknam, D. Saberi, Appl. Catal. A: Gen., 366 (2009) 220-225.
[26] N. Iravani, N.S. Mohammadzade, K. Niknam, Chin. Chem. Lett., 22 (2011) 1151-1154.
[27] S. Tayebi, M. Baghernejad, D. Saberi, K. Niknam, Chin. J. Catal., 32 (2011) 1477-1483.
[28] F. Rohandeh, D. Saberi, K. Niknam, Iran. J. Catal., 1 (2011) 71-78.
[29] S. Tayebi, K. Niknam, Iran. J. Catal., 2 (2012) 69-74.
[30] M. Baghernejad, K. Niknam, Int. J. Chem., 4 (2012) 52-60.
[31] S.P. Brojeni, M. Baghernejad, D. Saberi, K. Niknam, Green Chem. Lett. Rev., 6 (2013) 69-75.
[32] K. Niknam, A. Piran, Green Sustainable Chem. 3, (2013) 1-8.