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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

[EMIm][BH3CN] Ionic Liquid as an Efficient Catalyst for the Microwave- Assisted One-Pot Synthesis of Triaryl Imidazole Derivatives

Author(s): Rajesh K. Manjul, Suresh T. Gaikwad*, Vilas B. Gade*, Anjali S. Rajbhoj, Manohar K. Jopale, Shripad M. Patil, Dhananjay N. Gaikwad, Dayanand M. Suryavanshi, Santosh P. Goskulwad and Suvarna D. Shinde

Volume 20, Issue 10, 2023

Published on: 09 June, 2023

Page: [967 - 975] Pages: 9

DOI: 10.2174/1570178620666230510122033

Price: $65

Abstract

In this present investigation, efficient and general protocols for the synthesis of a series of imidazoles 4(a-p) derivatives have been developed by cyclocondensation of aromatic aldehydes, benzil and ammonium acetate in the existence of efficient [EMIm][BH3CN] ionic liquid catalyst under microwave condition in good to excellent yields (91-97%). The structures of the synthesized compounds have been confirmed by IR and NMR spectra. The significant features of this protocol are an uncomplicated workup process, rate enhancement with high yields, and efficient catalysts. It was concluded that [EMIm][BH3CN] is the finest catalyst under MW heating conditions.

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[1]
Ingale, A.P.; Patil, S.M.; Shinde, S.V. Tetrahedron Lett., 2017, 58(52), 4845-4848.
[http://dx.doi.org/10.1016/j.tetlet.2017.11.032]
[2]
Patil, S.; Tandon, R.; Tandon, N. Current Res. in Green. Sustain. Chem., 2021, 4, 100063.
[http://dx.doi.org/10.1016/j.crgsc.2021.100063]
[3]
Tandon, R.; Tandon, N.; Patil, S.M. RSC Adv., 2021, 11(47), 29333-29353.
[http://dx.doi.org/10.1039/D1RA03874E] [PMID: 35479579]
[4]
Patil, S. Int. J. Pharm. Res., 2021, 13(2), 2901-2905.
[http://dx.doi.org/10.31838/ijpr/2021.13.02.317]
[5]
Tandon, N.; Patil, S.M.; Tandon, R.; Kumar, P. RSC Advances, 2021, 11(35), 21291-21300.
[http://dx.doi.org/10.1039/D1RA02222A] [PMID: 35478786]
[6]
Patil, S.M.; Tandon, R.; Tandon, N. J. Phys. Conf. Ser., 2022, 2267(1), 012107.
[http://dx.doi.org/10.1088/1742-6596/2267/1/012107]
[7]
Tandon, R.; Patil, S.M.; Tandon, N. Lett. Org. Chem., 2022, 19(8), 616-626.
[http://dx.doi.org/10.2174/1570178619666220112112901]
[8]
Patil, S.M.; Ingale, A.P.; Pise, A.S.; Bhondave, R.S. ChemistrySelect, 2022, 7(26), e202201590.
[http://dx.doi.org/10.1002/slct.202201590]
[9]
Patil, S.M.; Tandon, R.; Tandon, N. ACS Omega, 2022, 7(28), 24190-24201.
[http://dx.doi.org/10.1021/acsomega.2c01107] [PMID: 35874196]
[10]
Gawande, M.B.; Shelke, S.N.; Zboril, R.; Varma, R.S. Acc. Chem. Res., 2014, 47(4), 1338-1348.
[http://dx.doi.org/10.1021/ar400309b] [PMID: 24666323]
[11]
Daştan, A.; Kulkarni, A.; Török, B. Green Chem., 2012, 14(1), 17-37.
[http://dx.doi.org/10.1039/C1GC15837F]
[12]
Kulkarni, A.; Török, B. Green Chem., 2010, 12(5), 875-878.
[http://dx.doi.org/10.1039/c001076f]
[13]
Chaudhari, A.S.; Parab, Y.S.; Patil, V.; Sekar, N.; Shukla, S.R. RSC Advances, 2012, 2(32), 12112-12117.
[http://dx.doi.org/10.1039/c2ra21803h]
[14]
Martinez-Palou, R. J. Mex. Chem. Soc., 2007, 51(4), 252-264.
[15]
Shirole, G.D.; Kadnor, V.A.; Tambe, A.S.; Shelke, S.N. Res. Chem. Intermed., 2017, 43(2), 1089-1098.
[http://dx.doi.org/10.1007/s11164-016-2684-7]
[16]
Lamberdino, J.G.; Wiseman, E.H. J. Med. Chem., 1974, 17(11), 1182-1188.
[http://dx.doi.org/10.1021/jm00257a011] [PMID: 4415171]
[17]
Zhang, C.; Sarshar, S.; Moran, E.J.; Krane, S.; Rodarte, J.C.; Benbatoul, K.D.; Dixon, R.; Mjalli, A.M.M. Bioorg. Med. Chem. Lett., 2000, 10(23), 2603-2605.
[http://dx.doi.org/10.1016/S0960-894X(00)00521-7] [PMID: 11128633]
[18]
Welton, T. Chem. Rev., 1999, 99(8), 2071-2084.
[http://dx.doi.org/10.1021/cr980032t] [PMID: 11849019]
[19]
Murthy, S.N.; Madhav, B.; Nageswar, Y.V.D. Tetrahedron Lett., 2010, 51(40), 5252-5257.
[http://dx.doi.org/10.1016/j.tetlet.2010.07.128]
[20]
Usyatinsky, A.Y.; Khmelnitsky, Y.L. Tetrahedron Lett., 2000, 41(26), 5031-5034.
[http://dx.doi.org/10.1016/S0040-4039(00)00771-1]
[21]
Wolkenberg, S.E.; Wisnoski, D.D.; Leister, W.H.; Wang, Y.; Zhao, Z.; Lindsley, C.W. Org. Lett., 2004, 6(9), 1453-1456.
[http://dx.doi.org/10.1021/ol049682b] [PMID: 15101765]
[22]
Siddiqui, S.A.; Narkhede, U.C.; Palimkar, S.S.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. Tetrahedron, 2005, 61(14), 3539-3546.
[http://dx.doi.org/10.1016/j.tet.2005.01.116]
[23]
Zang, H.; Su, Q.; Mo, Y.; Cheng, B.W.; Jun, S. Ultrason. Sonochem., 2010, 17(5), 749-751.
[http://dx.doi.org/10.1016/j.ultsonch.2010.01.015] [PMID: 20194046]
[24]
Wang, J.; Mason, R.; VanDerveer, D.; Feng, K.; Bu, X.R. J. Org. Chem., 2003, 68(13), 5415-5418.
[http://dx.doi.org/10.1021/jo0342020] [PMID: 12816512]
[25]
Sarshar, S.; Siev, D.; Mjalli, A.M.M. Tetrahedron Lett., 1996, 37(6), 835-838.
[http://dx.doi.org/10.1016/0040-4039(95)02334-8]
[26]
Kidwai, M.; Mothsra, P.; Bansal, V.; Somvanshi, R.K.; Ethayathulla, A.S.; Dey, S.; Singh, T.P. J. Mol. Catal. Chem., 2007, 265(1-2), 177-182.
[http://dx.doi.org/10.1016/j.molcata.2006.10.009]
[27]
Samai, S.; Nandi, G.C.; Singh, P.; Singh, M.S. Tetrahedron, 2009, 65(49), 10155-10161.
[http://dx.doi.org/10.1016/j.tet.2009.10.019]
[28]
Sivakumar, K.; Kathirvel, A.; Lalitha, A. Tetrahedron Lett., 2010, 51(22), 3018-3021.
[http://dx.doi.org/10.1016/j.tetlet.2010.04.013]
[29]
Shaabani, A.; Rahmati, A. J. Mol. Catal. Chem., 2006, 249(1-2), 246-248.
[http://dx.doi.org/10.1016/j.molcata.2006.01.006]
[30]
Lee, J.C.; Laydon, J.T.; McDonnell, P.C.; Gallagher, T.F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M.J.; Heys, J.R.; Landvatter, S.W.; Strickler, J.E.; McLaughlin, M.M.; Siemens, I.R.; Fisher, S.M.; Livi, G.P.; White, J.R.; Adams, J.L.; Young, P.R. Nature, 1994, 372, 739-746.
[http://dx.doi.org/10.1038/372739a0] [PMID: 7997261]
[31]
Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Burstell, H.; Sachse, B.U.S. Patent 4820335, 1989.
[32]
Antolini, M.; Bozzoli, A.; Ghiron, C.; Kennedy, G.; Rossi, T.; Ursini, A. Bioorg. Med. Chem. Lett., 1999, 9(7), 1023-1028.
[http://dx.doi.org/10.1016/S0960-894X(99)00112-2] [PMID: 10230632]
[33]
Wang, L.; Woods, K.W.; Li, Q.; Barr, K.J.; McCroskey, R.W.; Hannick, S.M.; Gherke, L.; Credo, R.B.; Hui, Y.H.; Marsh, K.; Warner, R.; Lee, J.Y.; Zielinski-Mozng, N.; Frost, D.; Rosenberg, S.H.; Sham, H.L. J. Med. Chem., 2002, 45(8), 1697-1711.
[http://dx.doi.org/10.1021/jm010523x] [PMID: 11931625]
[34]
Schmierer, R.; Mildenberger, H.; Buerstell, H. 1988.
[35]
Skonieczny, K.; Ciuciu, A.I.; Nichols, E.M.; Hugues, V.; Blanchard-Desce, M.; Flamigni, L.; Gryko, D.T. J. Mater. Chem., 2012, 22(38), 20649-20664.
[http://dx.doi.org/10.1039/c2jm33891b]
[36]
Khanna, I.K.; Weier, R.M.; Yu, Y.; Xu, X.D.; Koszyk, F.J.; Collins, P.W.; Koboldt, C.M.; Veenhuizen, A.W.; Perkins, W.E.; Casler, J.J.; Masferrer, J.L.; Zhang, Y.Y.; Gregory, S.A.; Seibert, K.; Isakson, P.C. J. Med. Chem., 1997, 40(11), 1634-1647.
[http://dx.doi.org/10.1021/jm9700225] [PMID: 9171873]
[37]
Grimmett, M.R.; Katritzky, A.R.; Rees, C.W., Eds.; Comrehensive Heterocyclic Chemistry; Pergamon Press: London, 1984.
[38]
Laufer, S.A.; Zimmermann, W.; Ruff, K.J. J. Med. Chem., 2004, 47(25), 6311-6325.
[http://dx.doi.org/10.1021/jm0496584] [PMID: 15566301]
[39]
Kantevari, S.; Snehalatha Nair, C.K.; Pardhasaradhi, M. J. Heterocycl. Chem., 2006, 43(5), 1353-1356.
[http://dx.doi.org/10.1002/jhet.5570430532]
[40]
Lantos, I.; Zhang, W.Y.; Shui, X.; Eggleston, D.S. J. Org. Chem., 1993, 58(25), 7092-7095.
[http://dx.doi.org/10.1021/jo00077a033]
[41]
Zhang, C.; Moran, E.J.; Woiwode, T.F.; Short, K.M.; Mjalli, A.M.M. Tetrahedron Lett., 1996, 37(6), 751-754.
[http://dx.doi.org/10.1016/0040-4039(95)02310-0]
[42]
Khosropour, A.R. Can. J. Chem., 2008, 86(3), 264-269.
[http://dx.doi.org/10.1139/v08-009]
[43]
Chary, M.V.; Keerthysri, N.C.; Vupallapati, S.V.N.; Lingaiah, N.; Kantevari, S. Catal. Commun., 2008, 9(10), 2013-2017.
[http://dx.doi.org/10.1016/j.catcom.2008.03.037]
[44]
Shaabani, A.; Rahmati, A.; Aghaaliakbari, B. Safaei-Ghomi. J. Synth. Commun., 2006, 36(1), 65-70.
[http://dx.doi.org/10.1080/00397910500328969]
[45]
Gade, V.B.; Rathi, A.K.; Bhalekar, S.B.; Tucek, J.; Tomanec, O.; Varma, R.S.; Zboril, R.; Shelke, S.N.; Gawande, M.B. ACS Sustain. Chem.& Eng., 2017, 5(4), 3314-3320.
[http://dx.doi.org/10.1021/acssuschemeng.6b03167]
[46]
Gade, V.; Goswami, A.; Varma, R.; Shelke, S.; Gawande, M. Nanomaterials , 2018, 8(4), 246.
[http://dx.doi.org/10.3390/nano8040246] [PMID: 29673159]
[47]
Chine, S.S.; Patil, C.S.; Gade, V.B. Curr. Catal., 2018, 7(3), 194-201.
[http://dx.doi.org/10.2174/2211544707666180918153941]
[48]
Gade, V.; Nilkanth, P.; Mhaske, G.; Manjul, R.; Shinde, V.; Kushare, S.; Shelke, S. IJIRSET, 2014, 3(7), 14339-14344.
[49]
Manjul, R.K.; Gade, V.B.; Gaikwad, D.N.; Suryavanshi, D.M.; Rajbhoj, A.S.; Gaikwad, S.T. Lett. Org. Chem., 2022, 19(6), 457-462.
[http://dx.doi.org/10.2174/1570178618666210405151600]
[50]
Rajbhoj, A.S.; Gaikwad, S.T.; Manjul, R.K.; Gade, V.B.; Gaikwad, D.N.; Suryavanshi, D.M. Lett. Org. Chem., 2022, 19(06), 457-462.

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