Abstract
Poly(4-vinylpyridinium butane sulfonic acid) hydrogen sulfate, P(4VPBSA)HSO4, a novel polymeric acidic catalyst, was easily prepared by reaction of cross-linked poly(4-vinylpyridine) with 1,4-butane sultone and further acidification of the catalyst with sulfuric acid. The catalyst was studied by FT-IR spectroscopy, scanning electron microscopy, and thermogravimetric analysis. The poly(ionic liquid) catalyst was shown to be an efficient dual acidic catalyst for one-pot preparation of 1,8-dioxo-octahydroxanthenes under solvent-free conditions. Reusability of the catalyst, easy work-up, eco-friendly reaction conditions, short reaction times, and high yields are some advantages of this procedure.
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References
D. Mecerreyes, Prog. Polym. Sci. 36, 1629 (2011)
J. Yuan, M. Antonietti, Polymer 52, 1469 (2011)
K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)
A. Kumar, R.A. Maurya, Tetrahedron 63, 1946 (2007)
M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64, 2375 (2008)
M.S. Singh, S. Chowdhury, RSC Adv. 2, 4547 (2012)
H.K. Wang, S.L. Morris-Natschke, K.H. Lee, Med. Res. Rev. 17, 367 (1997)
T Hideo Jpn Tokkyo Koho JP56005480 (CA 95 80922b) (1981)
J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 13, 67 (1978)
R. W. Lambert, J. A. Martin, J. H. Merrett, K. E. B. Parkes, G. J. Thomas, PCT Int. Appl. WO9706178 (CA 126 P212377y) (1997)
S. Hatakeyma, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun. 1202 (1988)
H. N. Karade, M. Sathe, M. P. Kaushik, Arkivoc xiii, 252 (2007)
S. Sato, Y. Naito, K. Aoki, Carbohydr. Res. 342, 913 (2007)
S. Kantevari, R. Bantu, L. Nagarapu, J. Mol. Catal. A: Chem. 269, 53 (2007)
P. Srihari, S.S. Mandal, J.S.S. Reddy, R. Srinivasa Rao, J.S. Yadav, Chin. Chem. Lett. 19, 771 (2008)
D. Fang, K. Gong, Z. Liu, Catal. Lett. 127, 291 (2009)
G. Karthikeyana, A. Pandurangan, J. Mol. Catal. A: Chem. 311, 36 (2009)
A. Javid, M.M. Heravi, F.F. Bamoharram, E. -J. Chem. 8(2), 910 (2011)
G.H. Mahdavinia, M.M. Ghanbari, H. Sepehrian, F. Kooti, J. Iran. Chem. Res. 3, 117 (2010)
J. Mondal, M. Nandi, A. Modak, A. Bhaumik, J. Mol. Catal. A: Chem. 363–364, 254 (2012)
F. Rashedian, D. Saberi, K. Niknam, J. Chin Chem, Soc. 57, 998 (2010)
A.R. Kiasat, M. Fallah-Mehrjardi, J. Braz. Chem. Soc. 19, 1595 (2008)
A.R. Kiasat, M. Fallah-Mehrjardi, Synth. Commun. 40, 1551 (2010)
Z.H. Zhang, Y.H. Liu, Catal. Commun. 9, 1715 (2008)
H. R. Shaterian, F. Rigi, Res. Chem. Intermed. doi 10.1007/s11164-013-1096-1
H. R. Shaterian, M Kangani, Res. Chem. Intermed. doi 10.1007/s11164-013-1097-0
Acknowledgments
We gratefully acknowledge support of this work by Shahid Chamran University Research Council. We are grateful to M. R. Fazeli-Mobarakeh for recording SEM images.
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Kiasat, A.R., Mouradzadegun, A. & Saghanezhad, S.J. Synthesis, characterization, and application of poly(4-vinylpyridinium butane sulfonic acid) hydrogen sulfate as a novel poly(ionic liquid) and heterogeneous solid acid catalyst for the preparation of 1,8-dioxo-octahydroxanthenes. Res Chem Intermed 41, 319–326 (2015). https://doi.org/10.1007/s11164-013-1194-0
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DOI: https://doi.org/10.1007/s11164-013-1194-0