ZrP2O7 NPs: A recyclable, efficient heterogeneous catalyst for the synthesis of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via a multi-component reaction

Document Type: Articles

Authors

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, 51167, Kashan, I.R. Iran.

Abstract

ZrP2O7 nanoparticles (NPs) as an efficient catalyst have been used for the preparation of 1,6-diamino-2- oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives via one-pot coupling of hyrazine hydrate, ethyl cyanoacetate, malononitrile and aromatic aldehydes under reflux conditions in ethanol. Using this method we obtained low reaction times, easy isolation of the targeted molecules, excellent yields.

Keywords


[1] G. Kirsch, S. Hesse, A. Comel, Curr. Org. Synth. 1 (2004) 47-63.
[2] K. Niknam, A. Jamali, M. Tajaddod, A. Deris, Chin. J. Catal. 33 (2012) 1312–1317.
[3] K. Niknam, R. Rashidian, A. Jamali, Sci. Iran. 20 (2013) 1863-1870.
[4] H. Shojaei, Z.L. Böhmer, P.V. Zezschwitz, J. Org. Chem. 72 (2007) 5091–5097.
[5] Q. Li, L.A. Mitscher, L.L. Shen, Med. Res. Rev. 20 (2000) 231-293.
[6] R.J. Cox, D. O’Hagan, J. Chem. Soc. Perkin Trans. 1 (1991) 2537-2540.
[7] M. Nagarajan, X.S. Xiao, S. Antony, G. Kohlhagen, Y. Pommier, M. Cushman, J. Med. Chem. 46 (2003) 5712-5724.
[8] L.A. Hasvold, W.B. Wang, S.L. Gwaltney, T.W. Rockway, L.T.J. Nelson, R.A. Mantei, S.A. Fakhoury, G.M. Sullivan, Q. Li, N.H. Lin, L. Wang, H. Zhang, J. Cohen, W.Z. Gu, K. Marsh, J. Bauch, S. Rosenberg, H.L. Sham, Bioorg. Med. Chem. Lett. 13 (2003) 4001-4005.
[9] S.V. Ryabukhin, A.S. Plaskon, D.M. Volochnyuk, A.A. Tolmachev, Synlett 13 (2004) 2287-2290.
[10] A. Kozikowski, G. Campiani, L.Q. Sun, Sh. Wang, A. Saxena, B.P. Doctor, J. Am. Chem. Soc. 118 (1996) 11357-11362.
[11] R.K. Beckman, J.C. Potenza, E.J. Enholm, J. Org. Chem. 52 (1987) 469-472.
[12] M.T. Cocco, C. Congiu, V. Lilliu, V. Onnis, Eur. J. Med. Chem. 40 (2005) 1365-1372.
[13] A. Domling, Chem. Rev. 106 (2006)17–89.
[14] A.H. Rezayan, C. R. Chim. 15 (2012) 499–503.
[15] A. Alizadeh, F. Movahedi, A.A. Esmaili, Tetrahedron Lett. 47 (2006) 4469-4471.
[16] H. Kefayati, F. Narchin, K. Rad-Moghadam, Tetrahedron Lett. 53 (2012) 4573–4575.
[17] M.B. Teimouri, F. Mansouri, R. Bazhrang, Tetrahedron 66 (2010) 259–264.
[18] D. Kumar, V.B. Reddy, Sh. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44 (2009) 3805–3809.
[19] N. Ahmed, J.E. Van Lier, Tetrahedron Lett. 47 (2006) 2725–2729.
[20] J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, A. Ziarati, Chin. Chem. Lett. 24 (2013) 921-925.
[21] S.B. Patil, P.R. Singh, M.P. Surpur, S.D. Samant, Synth. Commun. 37 (2007) 1659-1664.
[22] R.A. Sheldon, R.S. Downing, Appl. Catal. A: Gen. 189 (1999) 163-183.
[23] H. Hattori, Chem. Rev. 95 (1995) 537-558.
[24] J.S. Paul, R. Janssens, J.F.M. Denayer, G.V. Baron, P. A. Jacobs, J. Comb. Chem. 7 (2005) 407-413.
[25] J. Safaei-Ghomi, S. Zahedi, M.A. Ghasemzadeh, Iran. J. Cat. 2 (2012) 27-30.
[26] J. Safaei-Ghomi, H. Shahbazi-Alavi, A. Ziarati. R. Teymuri, M.R. Saberi, Chin. Chem. Lett. 25 (2014) 401-405.
[27] M. Kaneyoshi, J. Lumin. 121 (2006) 102-108.
[28] M. Seifi, M. Khajehasani Rabori, H. Sheibani, Mod. Res. Catal. 2 (2013) 8-12.
[29] C. Seoane, J.L. Soto, P, Zamorano, Org. Prep. Proc. Int. 16 (1984) 393-400.
[30] A. Javidan, A. Ziarati, J. Safaei-Ghomi, Ultra. Sonochem. 21 (2014) 1150-1154.