Abstract
Propylsulfonic acid functionalized Santa Barbara Amorphous-15 (SBA-15–Pr–SO3H) catalyst has been synthesized using a surface modification of mesoporous SBA-15 via the one-pot co-condensation method. The synthesized SBA-15–Pr–SO3H has been characterized by peculiar characterization techniques such as small- and wide-angle XRD, SEM–EDX, TEM, TG–DTA, acidity, FT-IR, Py-FT-IR and BET surface area analysis. The catalytic activity of synthesized catalyst has been studied towards solvent-free MW irradiation for the green and rapid synthesis of multi-substituted imidazoles, [2,4,5-triphenyl-1(H)-imidazole (tri-imidazole) and 1-benzyl-2,4,5-triphenyl-1H-imidazole (tetra-imidazole)]. The SBA-15–Pr–SO3H catalyst was found to be an efficient and recyclable solid acid catalyst and this solvent-free MW protocol afforded products in good to excellent yields of both, tri and tetra imidazoles (> 95%) within shorter reaction time (3 min) at 600 W as compared to the SBA-15 and other existing protocols. The applicability of this protocol was further explored by conducting the experiments in the presence of varied solvents and substituted aldehydes to generate a library of both, tri- and tetra-imidazole scaffolds. The catalyst was found to be reusable up to several runs without loss of its catalytic activity. This report allows the rapid and scalable access to a variety of multi-substituted imidazoles using SBA-15–Pr–SO3H, as heterogeneous catalyst.
Graphical abstract
SBA-15–Pr–SO3H catalyzed solvent-free MW assisted green synthesis of multi-substituted imidazoles via MCRs.
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References
J.P. Tierney, P. Lidstrom, B. Wathey, J. Westman, Tetrahedron 57, 9225 (2005)
D.M. D’Souza, T.J.J. Müller, Chem. Soc. Rev. 36, 1095 (2007)
A. Rivera-Hernández, I.S. López-Jimeno, G.A. Carmona-Reyes, R. Alfredo-Toscano, J.G. Penieres-Carrillo, C. Álvarez-Toledano, Tetrahedron Lett. 56, 4829 (2015)
J.J. Gabla, S.R. Mistry, K.C. Maheria, Catal. Sci. Technol. 7, 5154 (2017)
A.R. Karimi, Z. Alimohammadi, M.M. Amini, Mol. Divers. 14, 635 (2010)
B. Radziszewski, Chem. Ber. 15, 1493 (1882)
F. Japp, H. Robenson, Chem. Ber. 15, 1268 (1882)
G. Drefahl, H. Herma, Chem. Ber. 93, 486 (1960)
I. Lantos, W.Y. Zhang, X. Shui, D.S. Eggleston, J. Org. Chem. 58, 7092 (1993)
C. Zhang, E.J. Moran, T.F. Woiwode, K.M. Short, A.M.M. Mjalli, Tetrahedron Lett. 37, 751 (1996)
H. B. Lee, S. Balasubramanian, Org. Lett. 2, 323 (2000)
C.F. Claiborne, N.J. Liverton, K.T. Nguyen, Tetrahedron Lett. 39, 8939 (1998)
J.J. Gabla, S.R. Mistry, K.C. Maheria, J. Catal. Catal. 4, 20 (2017)
S. Balalaie, A. Arabanian, Green Chem. 2, 274 (2000)
M.C. Road, S. Nagar, M.L. Limited, A. Industrial, B. Village, J. Mandal, Rasayan J. Chem. 3, 335 (2010)
H.R. Shaterian, M. Ranjbar, J. Mol. Liq. 160, 40 (2011)
S.A. Siddiqui, U.C. Narkhede, S.S. Palimkar, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron 61, 3539 (2005)
J. Safari, S. Gandomi-ravandi, Z. Akbari, J. Adv. Res. 4, 509 (2013)
J. Wang, R. Mason, D. VanDerveer, K. Feng, X.R. Bu, J. Org. Chem. 68, 5415 (2003)
A. Shaabani, A. Rahmati, J. Mol. Catal. A Chem. 249, 246 (2006)
D. Morawala, A. Dalai, K.C. Maheria,J. Por. Mater. 26, (2018)
S.R. Mistry, K.C. Maheria, J. Catal. Catal. 1, 1 (2014)
S.R. Mistry, K.C. Maheria, J. Mol. Catal. A Chem. 355, 210 (2012)
S.R. Mistry, R.S. Joshi, K.C. Maheria, J. Chem. Sci. 123, 427 (2011)
S.R. Mistry, R.S. Joshi, S.K. Sahoo, K.C. Maheria, Catal. Lett. 141, 1541 (2011)
H. Chaudhuri, S. Dash, A. Sarkar, Ind. Eng. Chem. Res. 56, 2943 (2017)
L. Cao, Z. Jia, S. Ji, J. Hu, J. Nat. Gas Chem. 20, 377 (2011)
V.F. Vavsari, G. Mohammadi Ziarani, A. Badiei, RSC Adv. 5, 91686 (2015)
R.H. Vekariya, H.D. Patel, Synth. Commun. 45, 1031 (2015)
K.A. Shah, J.K. Parikh, K.C. Maheria, Catal. Today 237, 29 (2014)
A. Teimouri, A.N. Chermahini, J. Mol. Catal. A Chem. 346, 39 (2011)
S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65, 10155 (2009)
B. Maleki, H. Keshvari Shirvan, F. Taimazi, E. Akbarzadeh, Int. J. Org. Chem. 2, 93 (2012)
K. Babu, V. Surendhar, Hetero. Lett. 4, 235 (2014)
B.F. Mirjalili, A.H. Bamoniri, L. Zamani, Sci. Iran. 19, 565 (2012)
R. Yan, L. Ming, Z. Zong-Ze, Molecules 20, 20286 (2015)
N.M. Kalkhorani, M.M. Heravi,J. Chem. 1 (2013)
H.T. Najmeh Zahedi, A. Javid, M. Kazem Mohammadi, Bull. Chem. Soc. Ethiop. 32, 157 (2018)
K.F. Shelke, S.B. Sapkal, G.K. Kakade, B.B. Shingate, M.S. Shingare, Green Chem. Lett. Rev. 3, 27 (2010)
G.K. Sharma, N.K. Sharma, D. Pathak, Ind. J. Chem. 52B, 266 (2013)
Acknowledgements
The authors are grateful to the director, SVNIT, Surat, for providing research and financial assistance. This research was supported by a research grant for assistant professor No: Dean (R&C)/1503/2013-14 from Sardar Vallabhbhai National Institute of Technology, Surat (SVNIT, Surat). The authors would also like to thank IISER-Mohali, India, for SAXS characterization facility.
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Gabla, J.J., Lathiya, D.R., Revawala, A.A. et al. Propyl–SO3H functionalized SBA-15: Microwave-mediated green synthesis of biologically active multi-substituted imidazole scaffolds. Res Chem Intermed 45, 1863–1881 (2019). https://doi.org/10.1007/s11164-018-3707-3
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DOI: https://doi.org/10.1007/s11164-018-3707-3