Abstract
One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.
Keywords: One-pot synthesis, imidazolines, ethylenediamine, green chemistry, imidazolones, organic compounds.
Graphical Abstract
[http://dx.doi.org/10.1021/jm501100b] [PMID: 25255204]
[http://dx.doi.org/10.1002/adsc.201801471]
[http://dx.doi.org/10.1002/ajoc.201800619]
[http://dx.doi.org/10.1002/adsc.201800868]
[http://dx.doi.org/10.1002/adsc.201900599]
[http://dx.doi.org/10.1039/C8CY01418C]
[http://dx.doi.org/10.1016/j.tetlet.2014.11.046]
[http://dx.doi.org/10.3390/molecules25081909] [PMID: 32326131]
[http://dx.doi.org/10.2174/138527210791130488]
[http://dx.doi.org/10.1002/chem.200800271] [PMID: 18431735]
[http://dx.doi.org/10.1002/cmdc.202000048] [PMID: 32144846]
[http://dx.doi.org/10.1080/00397919008053197]
[http://dx.doi.org/10.1021/cr60170a002]
[http://dx.doi.org/10.1021/jo010868n] [PMID: 11975574]
[http://dx.doi.org/10.1002/adsc.200800797]
[http://dx.doi.org/10.1016/j.tetlet.2003.12.015]
[http://dx.doi.org/10.1016/j.bmcl.2005.07.083] [PMID: 16153828]
[http://dx.doi.org/10.1016/S0960-894X(02)00753-9] [PMID: 12419381]
[http://dx.doi.org/10.1016/S0197-0186(96)00039-3] [PMID: 9116584]
[http://dx.doi.org/10.1016/S0079-6468(08)70378-3] [PMID: 7905649]
[http://dx.doi.org/10.1016/j.bmc.2008.06.051] [PMID: 18621536]
[http://dx.doi.org/10.1016/S0163-7258(01)00170-X] [PMID: 11916539]
[http://dx.doi.org/10.2174/187152506775268758] [PMID: 16529547]
[http://dx.doi.org/10.1039/b700923b]
[http://dx.doi.org/10.1039/c2gc35644a]
[http://dx.doi.org/10.1002/anie.201100059] [PMID: 21374777]
[http://dx.doi.org/10.1021/cr2003954] [PMID: 22390139]
[http://dx.doi.org/10.2174/157017912803901619]
[http://dx.doi.org/10.1039/C4RA13506G]
[http://dx.doi.org/10.1021/cs400633a]
[http://dx.doi.org/10.1016/j.tet.2012.06.099]
[http://dx.doi.org/10.1039/C5SC02913A] [PMID: 28791118]
[http://dx.doi.org/10.1021/cr1002084] [PMID: 21105733]
[http://dx.doi.org/10.1039/B309033G ]
[http://dx.doi.org/10.1021/op0340311]
[http://dx.doi.org/10.1039/b506621m] [PMID: 16186917]
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746]
[http://dx.doi.org/10.1021/cr940277f ]
[http://dx.doi.org/10.1016/j.ccr.2004.05.012]
[http://dx.doi.org/10.2174/138527210793351599]
[http://dx.doi.org/10.2174/157017912803251747]
[http://dx.doi.org/10.1039/C8RA03338B ]
[http://dx.doi.org/10.2174/1570179412666150914200843]
[http://dx.doi.org/10.3184/030823516X14755061428199]
[http://dx.doi.org/10.1016/j.tet.2008.12.022]
[http://dx.doi.org/10.1039/C4DT02313G] [PMID: 25232889]
[http://dx.doi.org/10.1016/j.bmcl.2010.06.097]
[http://dx.doi.org/10.1021/jm020809h] [PMID: 12139447]
[http://dx.doi.org/10.1021/ol990623l ] [PMID: 10822552]
(b) Isobe, T.; Fukuda, K.; Araki, Y.; Ishikawa, T. Modified guanidines as chiral superbases: the first example of asymmetric silylation of secondary alcohols. Chem. Commun. (Camb.), 2001, 243, 243-244.
[http://dx.doi.org/10.1039/b009173l]
[http://dx.doi.org/10.1016/S0040-4039(00)73744-0]
(b) Jones, R.; Howard, K.J.; Snaith, J.S. Cycloaddition of homochiral imidazolinium ylides: a route to optically active pyrroloimidazoles. Tetrahedron Lett., 1996, 34, 1707-1710.
[http://dx.doi.org/10.1016/0040-4039(96)00113-X]
(c) Langlois, Y.; Dalko, P.I.J. Stereoselective synthesis of quaternary benzylic carbons using C2 symmetric imidazolines and tetrahydrofuran as electrophile. Org. Chem., 1998, 63(23), 8107-8117.
[http://dx.doi.org/10.1021/jo980289r]
[http://dx.doi.org/10.1016/S0960-894X(02)01076-4] [PMID: 12617911]
[http://dx.doi.org/10.1016/j.bmcl.2007.12.064] [PMID: 18191397]
[http://dx.doi.org/10.1016/j.bmcl.2007.12.023] [PMID: 18164978]
[http://dx.doi.org/10.1021/acs.orglett.8b00696] [PMID: 29553756]
[http://dx.doi.org/10.1021/jo980949s]
[http://dx.doi.org/10.1016/0010-938X(94)90160-0]
[http://dx.doi.org/10.1021/om020568b]
[http://dx.doi.org/10.1039/b904275j] [PMID: 19587941]
[http://dx.doi.org/10.1021/jm9608624] [PMID: 9371245]
[http://dx.doi.org/10.1002/med.2610060403 ]
[http://dx.doi.org/110.2174/1385272811317030010 ]
[http://dx.doi.org/10.1126/science.1092472] [PMID: 14704432]
[http://dx.doi.org/10.1016/j.tet.2016.08.040]
[http://dx.doi.org/10.1021/jo500790n] [PMID: 24820129]
[http://dx.doi.org/10.1016/j.tetlet.2014.07.030]
[http://dx.doi.org/10.1002/jhet.516]
[http://dx.doi.org/10.1080/00397910802109232]
[http://dx.doi.org/10.1016/j.tet.2006.11.007]
[http://dx.doi.org/10.1016/j.tetlet.2005.02.025]
[http://dx.doi.org/10.1021/jo200101q] [PMID: 21401025]
[http://dx.doi.org/10.1038/450810a] [PMID: 18064000]
[http://dx.doi.org/10.1038/469018a] [PMID: 21209638]
[http://dx.doi.org/10.1039/c0gc00797h]
[http://dx.doi.org/10.1039/C2RP90003C]
[http://dx.doi.org/10.1039/C1CS15222J] [PMID: 22048162]
[http://dx.doi.org/10.1039/b502713f]
[http://dx.doi.org/10.1039/C7RA11827A ]
[http://dx.doi.org/10.1071/CH13700]
[http://dx.doi.org/10.1016/j.tetlet.2005.10.134]
[http://dx.doi.org/10.1039/b007560o]
[http://dx.doi.org/10.1039/C8OB00535D] [PMID: 29651477]
[http://dx.doi.org/10.1016/j.tetlet.2010.02.030]
[http://dx.doi.org/10.1021/ol2022438] [PMID: 21992702]
(b) Li, D.; Ollevier, T. Synthesis of imidazolidinone, imidazolone, and benzimidazolone derivatives through oxidation using copper and air. Org. Lett., 2019, 21(10), 3572-3575.
[http://dx.doi.org/10.1021/acs.orglett.9b00973] [PMID: 31058508]
[http://dx.doi.org/10.2174/157018009787158553 ]
[http://dx.doi.org/10.1021/jo200789t] [PMID: 21639124]
[http://dx.doi.org/10.1021/acs.joc.6b02781] [PMID: 28055212]
[http://dx.doi.org/10.1039/C8OB03111H ]
[http://dx.doi.org/10.1021/jo060228q] [PMID: 16599610]
[http://dx.doi.org/10.3184/0308234041209112]
[http://dx.doi.org/10.1007/BF03245937]
[PMID: 10321453]
[http://dx.doi.org/10.2174/1570179412666150817221755 ]
[http://dx.doi.org/10.1016/j.ejmech.2014.11.028] [PMID: 25466925]
[http://dx.doi.org/10.1002/adsc.200600364]
[http://dx.doi.org/10.5650/jos.56.211] [PMID: 17898484]
[http://dx.doi.org/10.1021/jo01287a100]
[http://dx.doi.org/10.1002/jhet.114]
[http://dx.doi.org/10.1039/C7DT02883K] [PMID: 28891566]
[http://dx.doi.org/10.1016/j.tet.2012.01.086 ]
[http://dx.doi.org/10.1021/ol202402y] [PMID: 21988188]
[http://dx.doi.org/10.1016/S0040-4039(99)01580-4]
[http://dx.doi.org/10.1016/0040-4039(96)00930-6]
[http://dx.doi.org/10.3998/ark.5550190.0008.f14]