Synthesis of bis-thiazolidinones catalyzed by nano-NiZr4(PO4)6 under microwave irradiation

Document Type: Articles

Authors

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

2 Young Researchers and Elite Club, Kashan Branch, Islamic Azad University, Kashan, Iran.

Abstract

A rapid and efficient method for the synthesis of bis-thiazolidinones has been achieved by pseudo five-component reaction of aldehydes, ethylenediamine and thioglycolic acid in the presence of nano-NiZr4(PO4)6 as catalyst under microwave irradiation. Nano-NiZr4(PO4)6 has been characterized by powder X-ray diffraction, scanning electronic microscopy (SEM), energy dispersive spectroscopy (EDS), vibrating sample magnetometer (VSM), dynamic light scattering (DLS), thermogravimetric analysis (TGA) and FT-IR spectroscopy. In this research, microwave irradiation is used as a green and complementary technique for preparation of bis-thiazolidinones. Use of simple and readily available starting materials, excellent yields, short reaction times, reusability of the catalyst, low amount of catalyst and using of microwave as clean method are some advantages of this protocol.

Keywords


[1] J. Senkiv, N. Finiuk, D. Kaminskyy, D. Havrylyuk, M. Wojtyra, I. Kril, A. Gzella, R. Stoika, R. Lesyk, Eur. J. Med. Chem. 117 (2016) 33-46.
[2] H.M.A. Ashour, I.M. El-Ashmawy, A.E. Bayad, Monatsh. Chem. 147 (2016) 605-618.
[3] R. Nechak, S.A. Bouzroura, Y. Benmalek, L. Salhi, S.P. Martini, V. Morizur, E. Dunach, B.N. Kolli, Synth. Commun. 45 (2015) 262-672.
[4] D.D. Subhedar, M.H. Shaikh, M.A. Arkile, A. Yeware, D. Sarkar, B.B. Shingate, Bioorg. Med. Chem. Lett. 26 (2016) 1704-1708.
[5] M.V. Diurno O. Mazzoni, G. Correale, I.G. Monterrey, A. Calignano, G.L. Rana, A. Bolognese, Il Farmaco 54 (1999) 579–583.
[6] R.K. Rawal, Y.S. Prabhakar, S.B. Katti, E. De Clercq, Bioorg. Med. Chem. Lett. 13 (2005) 6771-6776.
[7] R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouque, E. De Clercq, Bioorg. Med. Chem. 15 (2007) 1725-1731.
[8] D. Kumar, M. Sonawane, B. Pujala, V.K. Jain, A.K. Chakraborti, Green Chem. 15 (2013) 2872-2884.
[9] S.P. Shrivastava, N. Seelam, R. Rai, J. Chem. 9 (2012) 825-831.
[10] A. Mobinikhaledi, A.K. Amiri, Lett. Org. Chem. 10 (2013) 764-769.
[11] R.M. Abdel-Rahman, T.E. Ali, Monatsh. Chem. 144 (2013) 1243-1252.
[12] J. Safaei‑Ghomi, P. Babaei, H. Shahbazi‑Alavi, S.G. Pyne, A.C. Willis, J. Iran. Chem. Soc. 13 (2016) 1439-1448.
[13] M.B. Gawande, S.N. Shelke, R. Zboril, R.S. Varma, Acc. Chem. Res. 47 (2014) 1338−1348.
[14] F.A. Bassyouni, S.M. Abu-Bakr, M.A. Rehim, Res. Chem. Intermed. 38 (2012) 283–322.
[15] J. Safaei-Ghomi, H. Shahbazi-Alavi, P. Babaei, H. Basharnavaz, S.G. Pyne, A.C. Willis, Chem. Heterocycl. Compd. 52 (2016) 288–293.
[16] M.B. Gawande, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42 (2013) 3371-3393.
[17] A. Dastan, A. Kulkarni, B. Torok, Green Chem. 14 (2012) 17–37.
[18] A. Sharma, P. Appukkuttan, E.V. Eycken, Chem. Commun. 48 (2012) 1623–1637.
[19] J. Safaei-Ghomi, E. Afkhami, H. Shahbazi-Alavi, A. Ziarati, Iran. J. Catal. 5 (2015) 321-326.
[20] N. Gorodylova, V. Kosinová, Z. Dohnalová, P. Sulcová. Dyes Pigm. 98 (2013) 393-404.
[21] J. Safaei-Ghomi, M. Asgari-Kheirabadi, H. Shahbazi-Alavi, A. Ziarati, Iran. J. Catal. 6 (2016) 319-324.
[22] I.G. Trubach, A.I. Beskrovnyi, A.I. Orlova, V.A. Orlova, V.S. Kurazhkovskaya, Crystallogr. Rep. 49 (2004) 895–898.
[23] A.R. Zaripov, V.A. Orlova, V.I. Petkov, O.M. Slyunchev, D.D. Galuzin, S.I. Rovnyi, Russ. J. Inorg. Chem. 54 (2009) 45-51.
[24] T. Previtera, M. Basile, M.G. Vigorita, G. Fenech, F. Occhiuto, C. Circosta, R.C. de Pasquale, Eur. J. Med. Chem. 22 (1987) 67-74.
[25] V.V. Kouznetsov, D.F. Amado, A. Bahsas, J. Amaro‐Luis, J. Heterocycl. Chem. 43 (2006) 447-452.