A simple and green method for the four-component synthesis of spiro[indoline-3,4'-pyrano[2,3-c]pyrazole using a new zeolite Y

Document Type : Original Article

Authors

School of Chemistry, Hakim Sabzevari University, Sabzevar, Iran

Abstract

Mn(II)/Pb(II)-exchanged zeolite Y was synthesized and characterized by XRD, EDX, FT-IR and SEM spectroscopies. This is the first application of Mn/Pb-Y in four-component synthesis of spiro[indoline-3,4'-pyrano[2,3-c]pyrazole from isatin, malononitrile, ethylacetoacetate and hydrazine hydrate as a heterogeneous acidic catalyst. Short reaction times, high yields of products and simple work-up procedure are the advantages of current method. The catalyst is inexpensive, can be easily prepared and can be recovered and reused.Short reaction times, high yields of products and simple work-up procedure are the advantages of current method. The catalyst is inexpensive, can be easily prepared and can be recovered and reused and reused.

Keywords

Main Subjects

References

[1] C. A. Winter, E. A. Risley, G. W. Nuss, J. Pharmacol. Exp. Ther. 141 (1963) 369.
[2] A. P. M. Bernardi, A. B. F. Ferraz, D. V. Albring, S. A. L. Bordignon, J. Schripsema, R. Bridi, C. S. Dutra-Filho, A. T.  Henriques, G. L. von Poser, J. Nat. Prod. 68 (2005) 784.
[3] L. E. Overman, M. D. Rosen, Angew. Chem. Int. Ed. 39 (2000) 4596.
[4] M. E. A. Zaki, H. A. Soliman, O. A. Hiekal and A. E. Z. Rashad, Naturforsch.C  61 (2006) 1.
[5] E. S. El-Tamany, F. A. El-Shahed, B. H. J. Mohamed, Serb. Chem. Soc. 64 (1999) 9.
[6] J. L. Wang, D. Liu, Z. J. Zhang, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci.97 (2000) 7124.
[7] M. Aitkin, D. Anderson, B. Francis, J. Hinde, “Statistical modelling in GLIM”, Clarendon Press; Oxford. (1989) 234.
[8] A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 124 (2002) 12964.
]9[ ثنایی شعار، هاله; توکلی، هامان; روﺋین، سارا، دانشگاه سمنان، مجله شیمی کاربردی، شماره 38 (1395) ص 139.
]10[ شوقی، مریم; سجادی خواه، سید سجاد، دانشگاه سمنان، مجله شیمی کاربردی، شماره 40 (1395) ص 99.
]11[ ملکی، بهروز; بقایری، مهدی; باعدی، جواد; صدیق اشرفی، سمانه، دانشگاه سمنان، مجله شیمی کاربردی، شماره 40 (1395) ص 107.
[12] Y. M. Litvinov, A. A. Shestopalov, L. A. Rodinovs Kaya,  A. M. Shestopalov, J. Comb. Chem. 11 (2009) 914.
[13] Y. Liu, Z. Ren, W. Cao, J. Chen, H. Deng and M. Shao, Synth. Commun. 41 (2011) 3620.
[14] A. Dandia, A. K. Jain, D. S. Bhati, Synth. Commun. 41 (2011) 2905.
[15] M. N. Elinson, A. S. Dorofeev, F. M. Miloserdov, G. I. Nikishin, Mol. Divers.13 (2009) 47.
[16] S. Ahadi, Z. Yasaei, A. Bazgir, J. Heterocycl. Chem. 47 (2010) 1090.
[17] M. Koohshari, M. Dabiri, P. Salehi, RCS Adv. 4 (2014) 10669.
[18] G. Gianneto, A. Montes, G. Rodrı´guez, “Zeolitas Caracterı´sticas, Propiedades y Aplicaciones Industriales”, Innovacio´n Tecnolo´ gica. Facultad de Ingenierı´a-UCV: Caracas (2000) pp. 305.
[19] J. A. Kaduk, J. Faber, Rigaku J. 12 (1995)14.
[20] S. F. Hojati, B. Maleki, Z. Beykzadeh, Monash. Chem. 142 (2011) 87.
[21] S. F. Hojati, S. A. Nezhadhoseiny, Z. Beykzadeh, Monash. Chem. 144 (2013) 387.
[22] S. F. Hojati, M. Gholizadeh, M. Haghdoust, F. Shafiezadeh, Bull. Korean Chem. Soc. 31(2010)3238
[23] S. F. Hojati, I. Mohammadpoor-Baltork, B. Maleki, M. Gholizadeh, F. Shafiezadeh, M. Haghdoust, Can. J. Chem. 85 (2010) 135.
[24] I. Mohammadpoor-Baltork, A. R. Khosropour, S. F. Hojati, Synlett (2005) 2747.
[25] I. Mohammadpoor-Baltork, A. R. Khosropour, S. F. Hojati, Catal. Commun. 8 (2007) 1865.
[26] I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, S. F. Hojati Catal. Commun. 9 (2008) 1153.
[27] B. Sulikowski, J. Phys. Chem. 97 (1993) 1420.
[28] E. Y. Choi, Y. Kim, Y. W. Han, K. Seff, Micropor. Mesopor. Mat. 41 (2000) 61.
[29] D. Base, K. Seff, Micropor. Mesopor. Mat. 33 (1999) 265.
[30] E. L. Pires, J. C. Magalhᾶes, U. Schuchardt, Appl. Catal. A: General. 203 (1999) 231.
[31] A. P. Bolton, Molecular Sieve Zeolite. Academic Press (1976).
[32] M. R. Maurya, A. K. Chandrakar, S. Chand, J. Mol. Catal. A: Chemical 263 (2007) 227.
[33] J. Feng, K. Ablajan, A. Sali, Tetrahedron 70 (2014) 484.
[34] Y. Zou, Y. Hu, H. Liu, D. Shi, ACS Comb. Sci. 14 (2012) 38.
Applied Chemistry Today
Volume 13, Issue 46
March 2018
Pages 311-326

Files

Share

How to cite

Statistics