Synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst

Iranian Journal of Catalysis

مقاله 2، دوره 6، شماره 4، آذر 2016، صفحه 319-324   

نوع مقاله: Articles

نویسندگان

Javad Safaei-Ghomi^{* 1}؛ Mehrnoosh Asgari-Kheirabadi¹؛ Hossein Shahbazi-Alvi¹؛ Abolfazl Ziarati²

¹Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I. R. Iran.

²School of Chemistry, College of Science, University of Tehran, Tehran 14155-6455, Iran.

چکیده

Nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst have been used for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates by the four component reaction of dimethylacetylenedicarboxylate, hydrazinehydrate, malononitrile and aromatic aldehydes in water at room temperature. In this research Nano-ZnZr4(PO4)6 coordinate with the active groups(particular C=O, C≡N and active H) thus increasing the activity of the groups. Also this nanoscale heterogeneous catalysts present higher surface areas which are mainly responsible for their catalytic activity. These surface atoms behave as the centers where the chemical reactions could be catalytically activated. The key advantages of this process are high yields, shorter reaction times, reusability of catalyst, easy work-up, milder reaction conditions and environmentally benign.

کلیدواژه‌ها

Nano-ZnZr4(PO4)6؛ Catalytic activity؛ Pyrano[2؛ 3-c]pyrazole؛ One-pot؛ Multicomponent reaction

مراجع

[1] N.R. Mohamed, N.Y. Khaireldin, A.F. Fahmy, A.A. El-Sayeda, Pharma. Chem. 2 (2010) 400-417.
[2] S.C. Kuo, L.J. Huang, H. Nakamura, J. Med. Chem. 27 (1984) 539-544.
[3] M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, A.E.Z. Rashad, Naturforsch. C61 (2006) 1-5.
[4] N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14 (2006) 4792-4802.
[5] F.M. Abdelrazek, P. Metz, N.H. Metwally, S.F. El-Mahrouky, Arch. Pharm. 339 (2006) 456-460.
[6] B. Myrboh, H. Mecadon, M.R. Rohman, M. Rajbangshi, I. Kharkongor, B.M. Laloo, I. Kharbangar, B. Kshiar, Org. Prep. Proc. Int. 45 (2013) 253-303.
[7] B. Jiang, T. Rajale, W. Wever, S.J. Tu, G. Li, Chem. Asian J. 5 (2010) 2318-2335.
[8] J. Safaei-Ghomi, H. Shahbazi-Alavi, M.R. Saberi-Moghadam, A. Ziarati, Iran. J. Catal. 4 (2014) 289-294.
[9] H. Fujioka, K. Murai, O. Kubo, Y. Ohba, Y. Kita, Org. Lett. 9 (2007) 1687-1690.
[10] M. Shankar Singh, S. Chowdhury, RSC Adv. 2 (2012) 4547–4592.
[11] J. P. Wan, Y. Liu, RSC Adv. 2 (2012) 9763-9777.
[12] G. Yanlong, Green Chem. 14 (2012) 2091–2128
[13] C.W. Lim, I.S. Lee, Nano Today 5 (2010) 412-434.
[14] K. Chanda, S. Rej, M. H. Huang, Chem. Eur. J. 19 (2013) 16036-16043.
[15] V. Polshettiwar, R.S. Varma, Green Chem. 12 (2012) 743-754.
[16] W. Long, C. S. Gill, S. Choi, C. W. Jones, Dalton Trans. 39 (2010) 1470-1472.
[17] J. Safaei-Ghomi, M.R. Saberi-Moghadam, H. Shahbazi Alavi, M. Asgari Kheirabadi, J. Chem. Res. 2014 (38) 583-585.
[18] N. Gorodylova, V. Kosinova, Z. Dohnalova, P. Belina, P. Sulcova, Dyes Pigm. 98 (2013) 393-404.
[19] D. M. Liu, Mater. Chem. Phys. 36 (1994) 350-353.
[20] H. Mecadon, M.R. Rohman, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 2523-2525.
[21] G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49 (2008) 5636-5638.
[22] A. Siddekha, A. Nizam, M.A. Pasha, Spectrochim. Acta Part A 81 (2011) 431-440.
[23] M.B. Madhusudana Reddy, V.P. Jayashankara, M.A. Pasha, Synth. Commun. 40 (2010) 2930-2934.
[24] H. Mecadon, M.R. Rohman, I. Kharbangar, B.M. Laloo, I. Kharkongor, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 3228-3231.
[25] A.M. Zonouz, I. Eskandari, H.R. Khavasi, Tetrahedron Lett. 53 (2012) 5519-5522.