Abstract
Ketemines represent an interesting class of organic intermediates that has undergone a regrowth as a consequence of recent extensions of copper catalyzed azide alkyne cycloaddition (Cu- AAC) to other synthetic fields. This review summarizes the most recent generation methods of ketimines from CuAAC reaction, highlighting chemical properties focused on the synthesis of cyclic compounds, among others, affording a general outlook towards the development of new biologically active compounds.
Keywords: Ketenimine, alkyne, azide, copper catalyzed azide alkyne cycloaddition.
Graphical Abstract
[http://dx.doi.org/10.1016/B0-08-044705-8/00281-8]
[http://dx.doi.org/10.1021/acs.joc.5b00466] [PMID: 26031425]
[http://dx.doi.org/10.1002/ejoc.201200383]
[http://dx.doi.org/10.1055/s-0029-1218558]
[http://dx.doi.org/10.1039/c2cs35159e] [PMID: 22833018]
[http://dx.doi.org/10.1039/a900288j]
[http://dx.doi.org/10.1021/jo402570t] [PMID: 24344764]
[http://dx.doi.org/10.1021/acs.orglett.7b01500] [PMID: 28609631]
[http://dx.doi.org/10.1055/s-0034-1379303]
[http://dx.doi.org/10.1002/anie.200604241] [PMID: 17397087]
[http://dx.doi.org/10.1021/jo800733p] [PMID: 18557650]
[http://dx.doi.org/10.1002/chem.201704689] [PMID: 29105172]
[http://dx.doi.org/10.1016/j.tet.2016.07.036]
[http://dx.doi.org/10.1021/acs.joc.9b01906] [PMID: 31550889]
[http://dx.doi.org/10.1021/acs.orglett.5b02798] [PMID: 26529179]
[http://dx.doi.org/10.1021/jo701565m] [PMID: 17985923]
[http://dx.doi.org/10.3390/molecules26123700] [PMID: 34204392]
[http://dx.doi.org/10.1002/asia.201100340] [PMID: 21748856]
[http://dx.doi.org/10.1021/ja0432968] [PMID: 15713069]
[http://dx.doi.org/10.1016/j.tetlet.2010.11.135]
[http://dx.doi.org/10.1039/C7OB00499K] [PMID: 28530734]
[http://dx.doi.org/10.1021/ol502541w] [PMID: 25226502]
[http://dx.doi.org/10.1021/jo802014g] [PMID: 18956843]
[http://dx.doi.org/10.1039/C8CC04699A] [PMID: 29987306]
[http://dx.doi.org/10.1021/ja312592e] [PMID: 23452168]
[http://dx.doi.org/10.1039/D0OB01963A] [PMID: 33107883]
[http://dx.doi.org/10.1016/j.tet.2018.09.056]
[http://dx.doi.org/10.1021/acs.orglett.0c03861] [PMID: 33443441]
[http://dx.doi.org/10.1039/C3CC47182A] [PMID: 24233059]
[http://dx.doi.org/10.1039/c0cc00941e] [PMID: 20577668]
[http://dx.doi.org/10.1021/jo100354h] [PMID: 20373817]
[http://dx.doi.org/10.1021/ol900023t] [PMID: 19209900]
[http://dx.doi.org/10.1002/adsc.201000400]
[http://dx.doi.org/10.1021/mz5003239] [PMID: 35590701]
[http://dx.doi.org/10.1021/ja056399e] [PMID: 16287290]
[http://dx.doi.org/10.15227/orgsyn.085.0131]
[http://dx.doi.org/10.1002/anie.200503805] [PMID: 16570330]
[http://dx.doi.org/10.1021/ol4028368] [PMID: 24171428]
[http://dx.doi.org/10.1021/acs.joc.1c00331] [PMID: 34137260]
[http://dx.doi.org/10.1002/ejoc.201403285]
[http://dx.doi.org/10.1021/ol702241e] [PMID: 17979278]
[http://dx.doi.org/10.1021/ol102775s] [PMID: 21299243]
[http://dx.doi.org/10.1007/s00706-020-02684-5]
[http://dx.doi.org/10.1007/s11030-012-9393-y] [PMID: 22983883]
[http://dx.doi.org/10.1016/j.tetlet.2015.05.030]
[http://dx.doi.org/10.3762/bjoc.10.125] [PMID: 24991276]
[http://dx.doi.org/10.1021/ol502302w] [PMID: 25167465]
[http://dx.doi.org/10.1002/asia.201200636] [PMID: 22997181]
[http://dx.doi.org/10.1021/acs.orglett.6b00964] [PMID: 27149101]
[http://dx.doi.org/10.1002/anie.201708138] [PMID: 29083519]
[http://dx.doi.org/10.1039/B310593H] [PMID: 14685332]
[http://dx.doi.org/10.1021/jo802289s] [PMID: 19032113]
[http://dx.doi.org/10.1002/1099-0690(200212)2002:24<4222:AID-EJOC4222>3.0.CO;2-M]
[http://dx.doi.org/10.1002/anie.200503936] [PMID: 16570331]
[http://dx.doi.org/10.1002/ejoc.201301244]
[http://dx.doi.org/10.1002/anie.201810679] [PMID: 30354011]
[http://dx.doi.org/10.1021/ol4010323] [PMID: 23668246]
[http://dx.doi.org/10.1039/C6RA20583F]
[http://dx.doi.org/10.1039/c2sc20109g]
[http://dx.doi.org/10.1039/c1ob05745f] [PMID: 21837338]
[http://dx.doi.org/10.1021/acs.joc.9b02760] [PMID: 31779304]
[http://dx.doi.org/10.1021/ol201653j] [PMID: 21790168]
[http://dx.doi.org/10.1002/adsc.201500636]
[http://dx.doi.org/10.1021/ol202164x] [PMID: 21992587]
[http://dx.doi.org/10.1021/ol4014359] [PMID: 23875790]
[http://dx.doi.org/10.1055/s-0031-1289740]
[http://dx.doi.org/10.1021/ol070485x] [PMID: 17381100]
[http://dx.doi.org/10.1016/j.tet.2013.09.033]
[http://dx.doi.org/10.1039/c2ob25226k] [PMID: 22402824]
[http://dx.doi.org/10.1002/adsc.201700635]
[http://dx.doi.org/10.1021/acsomega.8b01179] [PMID: 31458953]
[http://dx.doi.org/10.1002/adsc.201700044]
[http://dx.doi.org/10.1039/C8CC06868B] [PMID: 30474656]
[http://dx.doi.org/10.1016/j.tet.2011.08.067]
[http://dx.doi.org/10.1021/ol402996x] [PMID: 24191743]
[http://dx.doi.org/10.1021/jo300855f] [PMID: 22721359]
[http://dx.doi.org/10.1021/ol400219n] [PMID: 23521106]
[http://dx.doi.org/10.1016/j.tet.2018.12.005]
[http://dx.doi.org/10.1021/acs.orglett.9b00740] [PMID: 30939026]
[http://dx.doi.org/10.1021/acs.orglett.0c01012] [PMID: 32233500]
[http://dx.doi.org/10.1002/anie.201405331] [PMID: 24989824]
[http://dx.doi.org/10.1039/C5CC07511D] [PMID: 26442840]