A Novel Efficient Solid Acid Nanocatalyst for the Synthesis of 1'-Aryl-2'-(2-oxoindolin-3-yl)spiro[indoline-3,5'-pyrroline]-2,3'-dione Derivatives

Subject Areas :

کبری نیکوفر ¹ (استادیار شیمی آلی، گروه شیمی، دانشکده فیزیک و شیمی، دانشگاه الزهرا (س)، تهران، ایران)
زهرا خادمی ² (کارشناسی ارشد شیمی آلی، گروه شیمی، دانشکده فیزیک و شیمی، دانشگاه الزهرا (س)، تهران، ایران)
شیوا خانی ³ (کارشناسی ارشد شیمی آلی، گروه شیمی، دانشکده فیزیک و شیمی، دانشگاه الزهرا (س)، تهران، ایران)

Received: 2018-03-11 Accepted : 2018-08-11 Published : 2018-08-23

Keywords: Heterogeneous catalyst, Multi-component reaction, Nanocatalyst, One-pot reaction, Spiro compounds,

Abstract :

Para-toluene sulfonic acid embedded on nano silica )ρ-TSA@nano SiO2( has been synthesized via a simple procedure and characterized by fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), and scanning electron microscopy (SEM) techniques. The synthesized nanocatalyst has been utilized to accelerate the one-pot multicomponent condensation reaction of isatins, anilines, and acetone to obtain the corresponding 1'-aryl-2'-(2-oxoindolin-3-yl)spiro[indoline-3,5'-pyrroline]-2,3'-diones at water media under reflux conditions. Utilization of H2O as available and green solvent, excellent yields of products, short reaction times, avoidance of by-products which could be obtained via Aldol condensation of acetone, easily-handle, inexpensive, non-toxic, and heterogeneous nano acid catalyst are some advantageous of the reported method. The recovery and reusability of the nano catalyst has been examined for four runs without activity loss

References:

[1] Astruc, D.; Lu, F.; Aranzaes, J.R.; Angewandte Chemie International Edition 44(48), 7852-7872, 2005.

[2] Beletskaya, I.P.; Cheprakov, A.V.; Chemical Reviews 100(8), 3009-3066, 2000.

[3] Lewis, L.N.; Chemical Reviews 93(8), 2693-2730, 1993.

[4] Hosseini-Sarvari, M.; Catalysis Letters 141(2), 347-355, 2011.

[5] Koukabi, N.; Kolvari, E.; Khazaei, A.; Zolfigol, M.A.; Shirmardi-Shaghasemi, B.; Khavasi, H.R.; Chemical Communications 47(32), 9230-9232, 2011.

[6] Zhang, Q.; Luo, J.; Wei, Y.Y.; Green Chemistry 12(12), 2246-2254, 2010.

[7] Kotadia, D.A.; Soni, S.S.; J. [8] Majumder, S.; Borah, P.; Bhuyan, P.J.;  Tetrahedron Letters 55 (6), 1168-1170, 2014.

[9] Revathy, K.; Lalitha, A.; J. Iranian Chemical Society 12(11), 2045-2049, 2015.

[10] Karimi-Jaberi, Z.; Pooladian, B.; Green Chemistry Letters and Reviews 5(2), 187-193, 2012.

[11] Huang, Y.B.; Fu, Y.; Green Chemistry 15(5), 1095-1111, 2013. 

[12] Anuradha, V.; Srinivas, P.V.; Aparna, P.; Rao, J.M.;  Tetrahedron Letters 47(28), 4933-4935, 2006. 

[13] Jadidi, Kh.; Ghahremanzadeh, R.; Bazgir, A.; J. Combinatorial chemistry 11(3), 341-344, 2009.

[14] Giacometti, J.; Wolf, N.; Gomzi, Z.; Milin, C.;  Reaction Kinetics and Catalysis Letters 59(2), 235-240, 1996.

[15] Abdel-Rahman, A.H.; Keshk, E.M.; Hanna, M.A.; El-Bady, Sh.M.; Bioorganic & Medicinal Chemistry 12 (9), 2483-2486, 2004.

[16] Sebahar, P.R.; Williams, R.M.; J. American Chemical Society 122(20), 5666-5667, 2000.

[17] Liu, H.; Dou, G.; Shi, D.; J. Comb. Chem. 12 (5), 633-637, 2010.

[18] Shanmugam, P.; Viswambharan, B.; Selvakumar, K.; Madhavan, S.; Tetrahedron Letters 49(16), 2611-2615, 2008.

[19] Peng, J.; Ran, G.-Y.; Du, W.; Chen, Y.-Ch.;  Organic Letters 17(18), 4490-4493, 2015.

[20] Zhong, F.; Han, X.; Wang, Y.; Lu, Y.; Angewandte Chemie 123(35), 7983-7987, 2011.

[21] Da Silva, J.F.M.; Garden, S.J.; Pinto, A.C.; J. Brazilian Chemical Society 12(3), 273-324, 2001.

[22] Itoh, T.; Ishikawa, H.; Hayashi, Y.; Organic Letters 11(17), 3854-3857, 2009.

[23] Prathima, P.S.; Srinivas, K.; Balaswamy, K.; Arundhathi, R.; Reddy, G.N.; Sridhar, B.; Rao, M.M.; Likhar, P.R.; Tetrahedron Asymmetry 22(24), 2099-2103, 2011.

[24] Borada, M.A.; Bhoia, M.; Prajapatia, N.P.; Patela, H.D.; Synthetic Communications 44(7), 897-906, 2014.

[25] Mathur, G.; Nain, S.; Medicinal Chemistry 4(4), 417-427, 2014.

[26] Alizadeh, A., Mokhtari, J.; Helvetica Chimica Acta 94(7), 1315-1319, 2011.

[27] Yang, F.; Sun, J.; Gao, H.; Yan, Ch.G.; RSC Advance 5(41), 32786-32794, 2015.

[28] Periyaraja, S.; Shanmugam, P.; Mandal, A.B.; Kumar, T.S.; Ramamurthy, P.; Tetrahedron 69(48), 2891-2897, 2013.

[29] Alizadeh, A.; Moafi, L.; J. Chemical Research 39(8), 464-472, 2015.

[30] Nikoofar, K.; MoazzezDizgarani, Sh.; Monatshefte für Chemie 146 (8), 1161-1204, 2015.

[31] Ghanbari, Kh.; Nikoofar, K.; Monatshefte für Chemie 145(11), 1867-1871, 2014.

[32] Nikoofar, K.; Ghanbari, Kh.; Monatshefte für Chemie 146(12), 2021-2027, 2015.

[33] Nikoofar, K.; Arabian Journal of Chemistry 10(2), 283-287, 2017.

[34] Nikoofar, K.; Khalili, Z.; Zeitschrift für Naturforschung B. 71(1), 31-36, 2015.

[35] Nikoofar, K.; Haghighi, M.; Khademi, Z.; Arabian Journal of Chemistry, 2016, in Press. 

[36] Sun, Y.; Sun, J.; Yan, Ch.-G.; Tetrahedron Letters 53(28), 3647-3649, 2012.

[37] Nikoofar, K.; Khademi, Z.; Haghighi, M.; J. Chemical Science 128(11), 1805-1811, 2016.

[38] Azizian, J.; Fallah-Bagher-Shaidaei, H.; Kefayati, H.; Synthetic Communications 33(5), 789-793, 2003.