Abstract
Herein, we report the sulfonamide-functionalized covalent organic framework (COF-SO3H) prepared from melamine and terephthalaldehyde and subsequent sulfonation, as an acidic porous catalyst for the one-pot preparation of polyhydroquinoline and 1,4-dihydropyridine derivatives. COF-SO3H was characterized by FT-IR, EDX, TGA, SEM, XRD, and BET. This methodology offers several advantages including high yield, short reaction time, simple workup procedure, solvent-free conditions, ease of separation, and recyclability.
Graphic abstract
One-pot preparation of polyhydroquinoline and 1, 4-dihydropyridine derivatives
Similar content being viewed by others
References
X. Zhao, N. Yan, RSC Adv. 5, 69955 (2015)
A.P. Cote, A.I. Benin, N.W. Ockwig, M. O’Keeffe, A.J. Matzger, O.M. Yaghi, Science 310, 1166 (2005)
J.L. Segura, M.J. Mancheñ, F. Zamora, Chem. Soc. Rev. 45, 5635 (2016)
H. Ding, A. Mal, C. Wang, Mater. Chem. Front. 4, 113 (2020)
Z. Wang, S. Zhang, Y. Chen, Z. Zhang, S. Ma, Chem. Soc. Rev 49, 708 (2020)
S. Das, P. Heasman, T. Ben, S. Qiu, Chem. Rev. 117(3), 1515 (2017)
J.S.M. Lee, A.I. Cooper, Chem. Rev. 120(4), 2171 (2020)
S.K. Das, P. Bhanja, S.K. Kundu, S. Mondal, A. Bhaumik, A.C.S. Appl, Mater. Interfaces 10(28), 23813 (2018)
P. Bhanja, A. Palui, S. Chatterjee, Y.V. Kaneti, J. Na, Y. Sugahara, A. Bhaumik, Y. Yamauchi, A.C.S. Sustain, Chem. Eng. 8(6), 2423 (2020)
M.G. Schwab, B. Fassbender, H.W. Spiess, A. Thomas, X. Feng, K. Müllen, J. Am. Chem. Soc. 131, 7216 (2009)
X. Shujuan, Y. Wang, W. Li, Y. Ji, J. Chromatogr. 1602, 481 (2019)
Z. Xiang, D. Cao, J. Mater. Chem. 1, 2691 (2013)
H. Li, Q. Pan, Y. Ma, X. Guan, M. Xue, Q. Fang, Y. Yan, V. Valtchev, S. Qiu, J. Am. Chem. Soc. 138, 14783 (2016)
J. Zhang, X. Han, X. Wu, Y. Liu, Y. Cui, J. Am. Chem. Soc. 139, 8277 (2017)
H. Vardhan, A.M. Al-Enizi, A. Nafady, S. Ma, Nanoscale 11, 21679 (2019)
G. Zhang, X. Li, Q. Liao, Y. Liu, K. Xi, W. Huang, X. Jia, Nat. Commun. 9, 2785 (2018)
D. Jin, B. Wang, X. Wu, J. Li, M. Mu, L. Chen, transit. Met. Chem. 44, 689 (2019)
A.R. Kiasat, H. Almasi, S.J. Saghanezhad, Rev. Roum. Chim. 59, 61 (2014)
E. Rafiee, S. Eavani, S. Rashidzadeh, M. Joshaghani, Inorg. Chim. Acta 362, 3555 (2009)
M. Nikpassand, M. Mamaghani, K. Tabataba, Molecules 14, 1468 (2009)
R.A. Coburn, M. Wierzba, M.J. Suto, A.J. Solo, A.M. Triggle, D.J. Triggle, J. Med. Chem. 31, 2130 (1988)
V. Klusa, Drugs Future 20, 135 (1995)
R.G. Bretzel, C.C. Bollen, E. Maeser, K.F. Federlin, Drugs Future 17, 465 (1992)
J. Safari, S.H. Banitaba, S.D. Khalili, J. Mol. Catal. Chem. 335, 46 (2011)
A. Hantzsch, Ann. Chem. 1, 215 (1882)
G.V.M. Sharma, K.L. Reddy, P.S. Lakshmi, P.R. Krishna, Synthesis 2006, 55 (2006)
R. Sridhar, P.T. Perumal, Tetrahedron 61, 2465 (2005)
S.J. Ji, Z.Q. Jiang, J. Lu, T.P. Loh, Synlett 2004, 0831 (2004)
L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z.Y. Fan, H. Tian, C.T. Qian, Tetrahedron 61, 1539 (2005)
M.A. Chari, K. Syamasundar, Catal. Commun. 6, 624 (2005)
A. Dondoni, A. Massi, E. Minghini, V. Bertolasi, Tetrahedron 60, 2311 (2004)
N.N. Karade, V.H. Budhewar, S.V. Shinde, W.N. Jadhav, Lett. Org. Chem. 4, 16 (2007)
J.L. Donelson, R.A. Gibbs, S.K. De, J. Mol. Catal. A Chem. 256, 309 (2006)
M. Maheswara, V. Siddaiah, G.L.V. Damu, C.V. Rao, Arkivoc 2, 201 (2006)
S. Ko, M.N.V. Sastry, C. Lin, C.F. Yao, Tetrahedron Lett. 46, 5771 (2005)
M.H. Sayahi, S. Bahadorikhalili, S.J. Saghanezhad, M. Mahdavi, Res. Chem. Intermed. 44, 5241 (2018)
M.H. Sayahi, S. Bahadorikhalili, S.J. Saghanezhad, M.A. Miller, M. Mahdavi, Res. Chem. Intermed. 46, 491 (2020)
R.R. Harale, P.V. Shitre, B.R. Sathe, M.S. Shingare, Res. Chem. Intermed. 43, 3237 (2017)
J. Safaei-Ghomi, A. Ziarati, S. Zahedi, Chem. Sci. 124, 933 (2012)
S.M. Vahdat, F. Chekin, M. Hatami, M. Khavarpour, S. Baghery, Z. Roshan-Kouhi, Chin. J. Catal. 34, 758 (2013)
G.K.K. Reddy, C.S. Reddy, J.S. Yadav, Tetrahedron Lett. 44, 29 (2003)
M. Tajbakhsh, E. Alaee, H. Alinezhad, M. Khanian, F. Jahani, S. Khaksar, M. Tajbakhsh, Chin. J. Catal. 33, 1517 (2012)
R. Taheri-Ledari, J. Rahimi, A. Maleki, Ultrason. Sonochem. 59, 104737 (2019)
A. Khazaei, M. Tavasoli, V. Jamshidi, F.G. Ghalil, A.R. Moosavi-Zare, Appl. Org. Chem. 32, 4368 (2018)
M. Abedini, F. Shirini, M. Mousapour, Res. Chem. Intermed. 42, 2303 (2016)
S. Igder, A.R. Kiasat, M.R. Shushizadeh, Res. Chem. Intermed. 41(10), 7227 (2015)
T. Amoli, S.M. Baghbanian, Res. Chem. Intermed. 44, 3389 (2018)
H. Alinezhad, S. Mohseni Tavakkoli, Res. Chem. Intermed. 41, 5931 (2015)
M.M. Khan, S. Shareef, S. Khan, Saigal, S.C. Sahoo, Synth. Commun. 49, 2884 (2019)
Acknowledgements
The financial support of this work by the research council of Islamic Azad University of Ahvaz is greatly acknowledged.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Farsi, R., Mohammadi, M.K. & Saghanezhad, S.J. Sulfonamide-functionalized covalent organic framework (COF-SO3H): an efficient heterogeneous acidic catalyst for the one-pot preparation of polyhydroquinoline and 1,4-dihydropyridine derivatives. Res Chem Intermed 47, 1161–1179 (2021). https://doi.org/10.1007/s11164-020-04322-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-020-04322-5