Abstract
2-pyridones represents ubiquitous scaffolds often present in both natural products and pharmaceutical compounds. Due to their wide applications in medicinal chemistry, it is not surprising that the synthesis of 2-pyridone derivatives has attracted organic chemists for many years. This mini review focuses on the recent development in the multi-component synthesis of 2-pyridones for the period 2011 to 2021, particularly those that involve the three/four component reactions of activated methylene, aldehyde or ketone withdifferent intermediate materials under different conditions.
Keywords: Organic chemistry, heterocyclic compounds, 2-pyridone, one-pot synthesis, three/four component reaction, green synthesis.
Graphical Abstract
[http://dx.doi.org/10.1007/s10593-020-02789-z]
[http://dx.doi.org/10.1080/00397911.2018.1457698]
[http://dx.doi.org/10.1021/jo400162d] [PMID: 23547954]
[http://dx.doi.org/10.3390/molecules25081909] [PMID: 32326131]
[http://dx.doi.org/10.1007/s11030-015-9596-0] [PMID: 26055184]
[http://dx.doi.org/10.1007/s13738-012-0155-7]
[http://dx.doi.org/10.1016/j.jscs.2021.101259]
[http://dx.doi.org/10.1039/C7SC04509C] [PMID: 29629070]
[http://dx.doi.org/10.1080/00397911.2013.862836]
[http://dx.doi.org/10.1016/j.molstruc.2019.126926]
[http://dx.doi.org/10.1039/D1QO00350J]
[http://dx.doi.org/10.1016/j.bmcl.2021.127845] [PMID: 33571649]
[http://dx.doi.org/10.1016/j.bmc.2020.115549] [PMID: 32503692]
[http://dx.doi.org/10.1016/j.phytol.2021.03.003]
[http://dx.doi.org/10.1080/14786419.2016.1269091] [PMID: 28032511]
[http://dx.doi.org/10.1016/j.resp.2017.02.012] [PMID: 28238903]
[http://dx.doi.org/10.1016/j.ejca.2020.04.044] [PMID: 32534242]
[http://dx.doi.org/10.1021/acs.oprd.6b00163]
[http://dx.doi.org/10.1021/acsomega.0c04424] [PMID: 33251438]
[http://dx.doi.org/10.1016/j.arth.2021.03.030] [PMID: 33888386]
[http://dx.doi.org/10.1039/C4RA06619G]
[http://dx.doi.org/10.1016/S2214-109X(20)30312-0] [PMID: 33069301]
[http://dx.doi.org/10.1021/jm901237x] [PMID: 20000776]
[http://dx.doi.org/10.1021/acs.joc.6b01415] [PMID: 27484240]
[http://dx.doi.org/10.1016/j.jinorgbio.2016.05.005] [PMID: 27235273]
[http://dx.doi.org/10.1016/j.mehy.2020.110005] [PMID: 32575019]
[http://dx.doi.org/10.1016/j.cbi.2020.109348] [PMID: 33278462]
[http://dx.doi.org/10.1039/D0CC06834A] [PMID: 33185645]
[http://dx.doi.org/10.1007/s11030-019-09959-y] [PMID: 31093836]
[http://dx.doi.org/10.1007/s00706-010-0329-x]
[http://dx.doi.org/10.1016/j.tet.2011.07.020] [PMID: 32287421]
[http://dx.doi.org/10.1016/j.tet.2017.02.005]
[http://dx.doi.org/10.1039/D0OB01631D] [PMID: 32966520]
[http://dx.doi.org/10.1039/C1RA00807B]
[http://dx.doi.org/10.1016/j.tetlet.2011.10.029]
[http://dx.doi.org/10.1016/j.tetlet.2012.08.030]
[http://dx.doi.org/10.5012/jkcs.2013.57.4.476]
[http://dx.doi.org/10.1007/s11030-014-9522-x] [PMID: 24792225]
[http://dx.doi.org/10.1016/j.tetlet.2014.02.123]
[http://dx.doi.org/10.1055/s-0035-1560824]
[http://dx.doi.org/10.1080/00397911.2018.1468467]
[http://dx.doi.org/10.1002/ajoc.201700610]
[http://dx.doi.org/10.1039/C8RA05690K]
[http://dx.doi.org/10.1039/C9RA05975J]
[http://dx.doi.org/10.1039/C9OB02456E] [PMID: 31956881]
[http://dx.doi.org/10.1021/acscatal.0c00499]
[http://dx.doi.org/10.1007/s11164-020-04261-1]
[http://dx.doi.org/10.1007/s11030-021-10313-4] [PMID: 34528212]
[http://dx.doi.org/10.1016/j.cclet.2012.01.018]
[http://dx.doi.org/10.1016/j.tetlet.2012.04.010]
[http://dx.doi.org/10.1016/j.tet.2012.03.106]
[http://dx.doi.org/10.3390/molecules17088822] [PMID: 22832883]
[http://dx.doi.org/10.1039/C5GC01526J]
[http://dx.doi.org/10.1039/C6RA18661K]
[http://dx.doi.org/10.1016/j.dyepig.2015.09.017]
[http://dx.doi.org/10.3390/molecules23030619] [PMID: 29522435]
[http://dx.doi.org/10.1002/jhet.3128]
[http://dx.doi.org/10.1002/slct.201800606]
[http://dx.doi.org/10.1039/C8OB00860D] [PMID: 29785444]
[http://dx.doi.org/10.1021/acs.orglett.9b00171] [PMID: 30794425]
[http://dx.doi.org/10.1055/s-0037-1612077]
[http://dx.doi.org/10.1016/j.saa.2019.117861] [PMID: 31806479]
[http://dx.doi.org/10.1016/j.molstruc.2020.128798]
[http://dx.doi.org/10.1016/j.molstruc.2020.129136]
[http://dx.doi.org/10.3184/174751914X14109743944636]
[http://dx.doi.org/10.1007/s11164-016-2608-6]
[http://dx.doi.org/10.1080/10406638.2018.1559206]
[http://dx.doi.org/10.1080/00304948.2019.1615365]
[http://dx.doi.org/10.4103/1735-5362.213980] [PMID: 28974973]
[http://dx.doi.org/10.3390/molecules181214519] [PMID: 24287988]
[http://dx.doi.org/10.1002/ejoc.201300235]
[http://dx.doi.org/10.1016/j.tetlet.2013.10.054]
[http://dx.doi.org/10.1002/jhet.2227]
[http://dx.doi.org/10.1002/jhet.2631]
[http://dx.doi.org/10.1007/s42250-018-0021-9]
[http://dx.doi.org/10.1021/acsomega.9b02133] [PMID: 32258858]
[http://dx.doi.org/10.1016/j.ultsonch.2010.04.009] [PMID: 20510640]
[http://dx.doi.org/10.1007/s11164-012-0972-4]
[http://dx.doi.org/10.1002/jhet.1632]
[http://dx.doi.org/10.12816/0026450]
[http://dx.doi.org/10.1055/s-0035-1561429]
[http://dx.doi.org/10.1021/acs.joc.8b01788] [PMID: 30230328]
[http://dx.doi.org/10.1002/jhet.4175]