Abstract
Sulfonic acid-functionalized (SO3H-functionalized) mesoporous MCM-41 catalyst was synthesized by anchoring 3-((3-(trimethoxysilyl)propyl)thio)propane-1-sulfonic acid onto MCM-41-type silica and characterized by FT-IR spectroscopy, elemental analysis and scanning electron microscopy (SEM) techniques. The catalyst was used for the efficient multi-component synthesis of 1H-pyrazolo-[3,4-b]pyridines and spiro-pyrazolo-[3,4-b]pyridines. Notably, the catalyst could be recycled and reused with negligible loss in activity over seven cycles.
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L.F. Tietze, A. Modi, Med. Res. Rev. 20, 304–322 (2000)
I. Ugi, A. Dömling, W. Hörl, Endeavour 18, 115–122 (1994)
A. Domling, Chem. Rev. 106, 17–89 (2006)
K. Kumaravel, G. Vasuki, Curr. Org. Chem. 13, 1820–1841 (2009)
M. Chiouaa, A. Samadia, E. Sorianoa, O. Lozachb, L. Meijerb, J. Marco-Contelles, Bioorgan. Med. Chem. Lett. 19, 4566–4569 (2009)
D. Silva, M. Chioua, A. Samadi, M.C. Carreiras, M.-L. Jimeno, E. Mendes, C. de los Ríos, A. Romero, M. Villarroya, M.G. López, J. Marco-Contelles, Eur. J. Med. Chem. 46, 4676–4681 (2011)
K. Wilcoxen, C.Q. Huang, J.R. McCarthy, D.E. Grigoriadis, C. Chen, Biorg. Med. Chem. Lett. 13, 3367–3370 (2003)
T.E.S. Ali, Eur. J. Med. Chem. 44, 4385–4392 (2009)
H. Hoehn, I. Polacek, E. Schulze, J. Med. Chem. 16, 1340–1346 (1973)
K. Chavva, S. Pillalamarri, V. Banda, S. Gautham, J. Gaddamedi, P. Yedla, C.G. Kumar, N. Banda, Bioorg. Med. Chem. Lett. 23, 5893–5895 (2013)
I.H. Eissa, A.M. El-Naggar, M.A. El-Hashash, Bioorg. Chem. 67, 43–56 (2016)
Z. Yin, L. Yang, L. Wu, J. Chem. Sci. 125, 601–606 (2013)
P. Rosenmunnd, M. Hosseini-Merescht, C. Bub, Liebigs Ann. Chem. 1994, 151–158 (1994)
S. Crosignani, C. Jorand-Lebrun, P. Page, G. Campbell, V. Colovray, M. Missotten, Y. Humbert, C. Cleva, J.-F. Arrighi, M. Gaudet, Z. Johnson, P. Ferro, A. Chollet, A.C.S. Med, Chem. Lett. 2, 644–649 (2011)
T. Usui, M. Kondoh, C.-B. Cui, T. Mayumi, H. Osada, A. Tryprostatin, Biochem. J. 333, 543–548 (1998)
A.J. Crisci, M.H. Tucker, M.-Y. Lee, S.G. Jang, J.A. Dumesic, S.L. Scott, ACS Catal. 1, 719–728 (2011)
Q. Cai, W.Y. Lin, F.S. Xiao, W.Q. Pang, X.H. Chen, Microporous Mesoporous Mater. 8, 1–15 (1999)
M. Cai, J. Peng, W. Hao, G. Ding, Green Chem. 13, 190–196 (2011)
M. Selvaraj, P.K. Sinha, D.-W. Park, I. Kim, S. Kawi, C.S. Ha, Dalton Trans. 41, 14197–14203 (2012)
S. Kawi, S.C. Shen, P.L. Chew, J. Mater. Chem. 12, 1582–1586 (2002)
X. Sheng, J. Gao, L. Han, Y. Jia, W. Sheng, Microporous Mesoporous Mater. 143, 73–77 (2011)
M. Hajjami, F. Ghorbani, F. Bakhti, Appl. Catal. A: Gen 470, 303–310 (2014)
S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Catal. Sci. Technol. 3, 2717–2722 (2013)
S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Adv. Synth. Catal. 345, 3095–3104 (2012)
S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, R. Kia, RSC Adv. 2, 5610–5616 (2012)
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The authors are grateful to the Centre of Excellence of Chemistry and Research Council of the University of Isfahan for financial support of this work.
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Safaei, S., Mohammadpoor-Baltork, I., Khosropour, A.R. et al. SO3H-functionalized MCM-41 as an efficient catalyst for the combinatorial synthesis of 1H-pyrazolo-[3,4-b]pyridines and spiro-pyrazolo-[3,4-b]pyridines. J IRAN CHEM SOC 14, 1583–1589 (2017). https://doi.org/10.1007/s13738-017-1099-8
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DOI: https://doi.org/10.1007/s13738-017-1099-8