One-pot and efficient synthesis of triazolo[1,2-a]indazole-triones catalyzed by poly(ethylene glycol) based magnetic dicationic ionic liquid
الموضوعات : Iranian Journal of CatalysisBijan Mombeni Goodajdar 1 , Soghra Soleimani 2
1 - Department of Chemistry, Islamic Azad University Omidiyeh Branch, Omidiyeh, Iran.
2 - Department of Chemistry, Islamic Azad University Omidiyeh Branch, Omidiyeh, Iran.
الکلمات المفتاحية: Dimedone, One-pot, Urazole, Magnetic dicationic ionic liquid, polyethylene glycol,
ملخص المقالة :
An atom-efficient, eco-friendly, solvent-free, high yielding, multicomponent green strategy to synthesize triazolo[1,2-a]indazole-triones derivatives by the one-pot condensation of aldehyde, dimedone, and phenyl urazole is presented. A series of different substituted aromatic aldehydes including either electron-withdrawing or electron-donating groups used in this reaction participated well and gave the corresponding products in good to excellent yield. Poly (ethylene glycol) based magnetic room temperature dicationic ionic liquid, PEG-MRTDIL, was prepared by mixing PEG-DIL with anhydrous FeBr3 under neat conditions. The catalyst was studied by UV and IR spectroscopy. This method provides several advantages such as environment benign, high yield, simple work up procedure and reusable catalyst.
[1] (a) E.J. Noga, G.T. Barthalmus, M.K. Mitchell, Cell Biol. Int. Rep. 10 (1986) 239-247. (b) P.N. Craig, Comprehensive Medicinal Chemistry, C.J. Drayton, Ed.; Pergamon Press, New York, USA, 1991.
[2] R.A. Izydore, I.H. Hall, U.S. Patent (1989) 4866058.
[3] K.C. Joshi, P. Chand. Pharmazie 37 (1982) 864-865.
[4] A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna, S.M. El-Bady, Bioorg. Med. Chem. 12 (2006) 2483-2488.
[5] T.H. Kang, K. Matsumoto, Y. Murakami, H. Takayama, M. Kitajima, N. Aimi and H. Watanabe, Eur. J. Pharmacol. 444 (2002) 39–45.
[6] (a) M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64 (2008) 2375-2378. (b) H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A 345 (2008) 128-133. (c) H.R. Shaterian, A. Hosseinian, M. Ghashang, ARKIVOC 2 (2009) 59-67. (d) J.M. Khurana, D. Magoo, Tetrahedron Lett. 50 (2009) 7300-7303. (e) M. Adharvana Chari, G. Karthikeyan, A. Pandurangan, T. Siddulu Naidu, B. Sathyaseelan, S.M. Javaid Zaidi, A. Vinu, Tetrahedron Lett. 51 (2010) 2629-2632. (f) A. Hasaninejad, A. Zare, M. Shekouhy, Tetrahedron 67 (2011) 390-400. (g) D. Azaria, R. Nejat-Yami, Z. Akrami, F. Sameri, S. Samadi, Lett. Org. Chem. 9 (2012) 128-132. (h) A. Bazgir, M. Seyyedhamzeh, Z. Yasaei, P. Mirzaei, Tetrahedron Lett. 48 (2007) 8790-8794. (i) A. Khazaei, M.A. Zolfigol, T. Faal-Rastegar, G. Chehardol, S. Mallakpour, Iran. J. Catal. 3 (2013) 211-220.
[7] H.R. Shaterian, F. Khorami, A. Amirzadeh, R. Doostmohammadi, M. Ghashang, J. Iran. Chem. Res. 2 (2009) 57.
[8] M.F. Hoover, J. Macromol. Sci. Chem. 4 (1970)1327-418.
[9] S.M. Hamid, D.C. Sherrington, Polymer 28 (1987) 325-331.
[10] S.M. Hamid, D.C. Sherrington, Polymer 28 (1987) 332-339.
[11] J. Tang, M. Radosz, Y. Shen, Macromolecules 41 (2008) 493-496.
[12] (a) Y.L. Wang, J. Luo, Z.L. Liu, J. Chin. Chem. Soc. 60 (2013) 1007-1013. (b) Y.L. Wang, J. Luo, T.J. Hou, Z.L. Liu, Aust. J. Chem. 66 (2013) 586-593. (c) J. Luo, T.T. Xing, Y.L. Wang, New J. Chem. 37 (2013) 269-273.
[13] Y.L. Wang, Z. Li, J. Luo, Z.L. Liu, J. Chin. Chem. Soc. 60 (2013) 1431-1436.
[14] (a) B.M. Godajdar, A.R. Kiasat, M.M. Hashemi, J. Mol. Liq. 183 (2013) 14-19. (b) B.M. Godajdar, A.R. Kiasat, M.M. Hashemi, Heterocycles 87 (2013) 559-570. (c) B.M. Godajdar, A.R. Kiasat, J. Chil. Chem. Soc. 58 (2013) 1850-1853. (d) B.M. Godajdar, S. Soleimani, J. Chin. Chem. Soc. 61 (2014) 447-452.
[15] W. Ye, H. Jiang, X.C. Yang, Chem. Sci. 123 (2011) 331–334.
[16] A.M. Boldi, C.R. Johnson, H.O. Eissa, Tetrahedron Lett. 40 (1999) 619-622.
[17] Y. Arroya, J.F. Rodriguez, M. Santos, M.A. Sanz Tejedor, I. Vaco, R.J.L. Garcia, Tetrahedron: Asymmetry 15 (2004) 1059-1063.
[18] A. Hassankhani, E. Mosaddegh, S.Y. Ebrahimipour, Arabian J. Chem. (2011) DOI:10.1016/j.arabjc.2011. 10.003.
[19] D.R. Chandam, A.G. Mulik, P.P. Patil, S.D. Jagdale, D.R. Patil, M.B. Deshmukh, Res. Chem. Intermed. 41 (2015) 761-771.
