Abstract
Multiheteroatom-containing small-sized cyclic molecules such as 2- iminothiazolidines are often found to possess beneficial pharmacological properties. In this review article, the biological significance of 2-iminothiazolidines is discussed and the literature reports published in the last 15 years spanning from 2006 to 2020 describing various preparative routes to access 2-iminothiazolidine derivatives have been categorically and chronologically described. The notable synthetic methods discussed here involve ringexpansion transformations of nonactivated and activated aziridines, thiiranes, epoxides, and other miscellaneous reactions.
Keywords: 2-Iminothiazolidine, aziridine, thiirane, condensation, dominoring-opening cyclization, ring expansion.
Graphical Abstract
[http://dx.doi.org/10.1006/abio.1998.2596] [PMID: 9570840]
[http://dx.doi.org/10.1080/00304940409355393]
[PMID: 13278352]
[http://dx.doi.org/10.1248/jhs1956.40.61]
[http://dx.doi.org/10.1135/cccc19920415]
[http://dx.doi.org/0.1002/ddr.430220410 ]
[http://dx.doi.org/10.1016/j.vascn.2004.11.005] [PMID: 16125625]
[http://dx.doi.org/10.1269/jrr.42.401] [PMID: 11951663]
[http://dx.doi.org/10.1269/jrr.43.293] [PMID: 12518989]
[http://dx.doi.org/10.1002/ps.727] [PMID: 12974353]
[http://dx.doi.org/10.1016/j.ica.2010.11.037]
[http://dx.doi.org/10.1016/j.jfluchem.2005.10.016]
[http://dx.doi.org/10.1007/BF00471632]
[http://dx.doi.org/10.1016/j.tet.2005.09.028]
[http://dx.doi.org/10.1002/adsc.201401026]
[http://dx.doi.org/10.1002/chem.201303699] [PMID: 24604740]
[http://dx.doi.org/10.1002/anie.201207746] [PMID: 23165819]
[http://dx.doi.org/10.1002/chem.200400543] [PMID: 15515101]
[http://dx.doi.org/10.1002/ejoc.201300266]
[http://dx.doi.org/10.1002/chin.200340143 ]
[http://dx.doi.org/10.1016/j.jfluchem.2004.10.007]
[http://dx.doi.org/10.1021/jo00110a056]
[http://dx.doi.org/10.1021/jo048486f] [PMID: 15624926]
[http://dx.doi.org/10.1021/jo801703h] [PMID: 18942793]
[http://dx.doi.org/10.1016/S0040-4039(03)01457-6]
[http://dx.doi.org/10.1016/j.tet.2014.07.044]
[http://dx.doi.org/10.1016/j.tet.2006.04.058]
[http://dx.doi.org/10.1021/ja00121a026]
[http://dx.doi.org/10.1021/jo00799a609]
[http://dx.doi.org/10.1002/cber.19891221232]
[http://dx.doi.org/10.1007/7081_2015_159]
[http://dx.doi.org/10.1021/cr400582d] [PMID: 24773209]
[http://dx.doi.org/10.1039/C1CS15140A] [PMID: 21894345]
[http://dx.doi.org/10.1002/anie.200805542] [PMID: 19173352]
[http://dx.doi.org/10.1021/cr0680033] [PMID: 17488062]
[http://dx.doi.org/10.1002/3527607862.ch7]
[http://dx.doi.org/10.1021/ar050038m] [PMID: 16548508]
[http://dx.doi.org/10.1016/j.tet.2004.01.042]
[http://dx.doi.org/10.1039/B006015L] [PMID: 12357722]
[http://dx.doi.org/10.1039/C9CY01967G]
[http://dx.doi.org/10.1055/s-0039-1690875]
[http://dx.doi.org/10.1016/j.tet.2010.01.077]
[http://dx.doi.org/10.1021/cr400543u] [PMID: 24678905]
[http://dx.doi.org/10.1021/cr500036t] [PMID: 24869559]
[http://dx.doi.org/10.1039/c4cc02206h] [PMID: 24827993]
[http://dx.doi.org/10.1002/adsc.201700888]
[http://dx.doi.org/10.1002/slct.201800170]
[http://dx.doi.org/10.1007/s11030-018-9829-0] [PMID: 29728870]
[http://dx.doi.org/10.1021/acs.orglett.9b02058] [PMID: 31334664]
[http://dx.doi.org/10.1016/j.tet.2013.02.065]
[http://dx.doi.org/10.1002/chem.201204485] [PMID: 23512331]
[http://dx.doi.org/10.1039/c3ob40222c] [PMID: 23515632]
[http://dx.doi.org/10.1002/ajoc.201200070]
[http://dx.doi.org/10.3762/bjoc.8.43] [PMID: 22509208]
[http://dx.doi.org/10.1002/anie.201204224] [PMID: 22945340]
[http://dx.doi.org/10.1007/s00726-011-0879-1] [PMID: 21424811]
[http://dx.doi.org/10.1021/ol200348k] [PMID: 21384826]
[http://dx.doi.org/10.1016/j.ejmech.2010.11.037] [PMID: 21183259]
[http://dx.doi.org/10.1021/jo102285z] [PMID: 21291173]
[http://dx.doi.org/10.1021/jo200711s] [PMID: 21797274]
[http://dx.doi.org/10.1021/ja201492x] [PMID: 21443197]
[http://dx.doi.org/10.1021/ol100755v] [PMID: 20441205]
[http://dx.doi.org/10.1021/ol101584z] [PMID: 20812750]
[http://dx.doi.org/10.1039/B816617J] [PMID: 19081956]
[http://dx.doi.org/10.1126/science.1180739] [PMID: 20019280]
[http://dx.doi.org/10.1002/anie.200804415] [PMID: 19021173]
[http://dx.doi.org/10.1039/b821650a] [PMID: 19194575]
[http://dx.doi.org/10.1021/ja8036965] [PMID: 18616245]
[http://dx.doi.org/10.1039/b812369a] [PMID: 19082146]
[http://dx.doi.org/10.1021/ja0758077] [PMID: 17973389]
[http://dx.doi.org/10.1021/jo060313y] [PMID: 16749806]
[http://dx.doi.org/10.1021/ol035036l] [PMID: 12889910]
[http://dx.doi.org/10.1055/s-2002-34842]
[http://dx.doi.org/10.1021/jo0103571] [PMID: 11511255]
[http://dx.doi.org/10.1002/1099-0690(200010)2000:19<3337:AID-EJOC3337>3.0.CO;2-V]
[http://dx.doi.org/10.1002/chem.201504853] [PMID: 26891167]
[http://dx.doi.org/10.1039/C4OB02615B] [PMID: 25598487]
[http://dx.doi.org/10.1039/c2ob07062f] [PMID: 22410956]
[http://dx.doi.org/10.1021/ol203114a] [PMID: 22217034]
[http://dx.doi.org/10.1021/jo102267h] [PMID: 21194209]
[http://dx.doi.org/10.1002/chem.201002502] [PMID: 21438040]
[http://dx.doi.org/10.1021/ol102394h] [PMID: 21049948]
[http://dx.doi.org/10.1021/jo101916e] [PMID: 21070034]
[http://dx.doi.org/10.1021/ol902550q] [PMID: 20017499]
[http://dx.doi.org/10.1039/b916664e] [PMID: 20024103]
[http://dx.doi.org/10.1021/ol9024919] [PMID: 19894720]
[http://dx.doi.org/10.1016/j.tet.2007.03.116]
[http://dx.doi.org/10.1039/b804246m] [PMID: 18480901]
[http://dx.doi.org/10.1039/C6RA04923K]
[http://dx.doi.org/10.1021/acs.orglett.0c02801] [PMID: 32985195]
[http://dx.doi.org/10.1021/acs.joc.7b03033] [PMID: 29342362]
[http://dx.doi.org/10.1021/jo01268a009] [PMID: 5641025]
[http://dx.doi.org/10.1021/ja00083a007]
[http://dx.doi.org/10.1021/jo000608q] [PMID: 10987917]
[http://dx.doi.org/10.1002/jhet.5570080309]
[http://dx.doi.org/10.1107/S0108768110040760] [PMID: 21099029]
[http://dx.doi.org/10.1055/s-0036-1588670]
[http://dx.doi.org/10.1021/jo300002u] [PMID: 22448664]
[http://dx.doi.org/10.1021/jo500888j] [PMID: 24955856]
[http://dx.doi.org/10.1002/ajoc.201500224]
[http://dx.doi.org/10.1002/slct.201602062]
[http://dx.doi.org/10.1021/acs.orglett.7b01397] [PMID: 28613075]
[http://dx.doi.org/10.1021/acs.joc.6b01919] [PMID: 27704829]
[http://dx.doi.org/10.1002/ejoc.201700506]
[http://dx.doi.org/10.1021/acs.orglett.8b00986] [PMID: 29738257]
[http://dx.doi.org/10.1039/C8CC04249G] [PMID: 29951688]
[http://dx.doi.org/10.1055/s-0039-1691596]
[http://dx.doi.org/10.1039/C8OB00228B] [PMID: 29619472]
[http://dx.doi.org/10.2174/1385272823666191007163310]
[http://dx.doi.org/10.1002/jhet.5570060526]
[http://dx.doi.org/10.1021/jo061239m] [PMID: 16958545]
[http://dx.doi.org/10.1039/C4RA08902B]
[http://dx.doi.org/10.1055/s-0034-1379949]
[http://dx.doi.org/10.1055/s-0032-1317162]
[http://dx.doi.org/10.1021/acs.joc.6b01551] [PMID: 27425856]
[http://dx.doi.org/10.1021/acs.joc.6b02190] [PMID: 27731640]
[http://dx.doi.org/10.1007/s00706-015-1543-3]
[http://dx.doi.org/10.3184/174751916X14656621014049]
[http://dx.doi.org/10.1016/j.tetlet.2017.05.048]
[http://dx.doi.org/10.1126/science.aav9713] [PMID: 31048464]
[http://dx.doi.org/110.24820/ark.5550190.p010.246 ]
[http://dx.doi.org/10.1021/acssuschemeng.7b04723]
[http://dx.doi.org/10.1039/C7CC09151F] [PMID: 29326995]
[http://dx.doi.org/10.1021/acs.orglett.7b03128] [PMID: 29076336]
[http://dx.doi.org/10.1002/ajoc.201800274]
[http://dx.doi.org/10.1039/C7OB02915B] [PMID: 29260830]
[http://dx.doi.org/10.1016/j.tetasy.2006.05.009]
[http://dx.doi.org/10.1134/S1070363206070231]
[http://dx.doi.org/10.1070/MC2006v016n04ABEH002211]
[http://dx.doi.org/10.1007/s11172-006-0472-z]
[http://dx.doi.org/10.1021/ja9066354] [PMID: 19778019]
[http://dx.doi.org/10.1107/S160053681200832X] [PMID: 22589992]
[http://dx.doi.org/10.1016/j.tet.2012.06.084]
[http://dx.doi.org/10.1016/j.tetlet.2014.01.085]
[http://dx.doi.org/10.1039/C8CC05311A] [PMID: 30043018]
[http://dx.doi.org/10.4067/S0717-97072019000204441]
[http://dx.doi.org/10.1039/C9OB00625G] [PMID: 31062809]
[http://dx.doi.org/10.1038/s41557-019-0225-x] [PMID: 30936523]