Abstract
The manuscript describes a facile and an efficient methodology for the synthesis of 1, 3, 4 trisubstituted-β-lactams by base mediated oxa-Michael addition reactions of 3-hydroxy-2- azetidinones with acetylenic esters under different reaction conditions. These functionalized 1, 3, 4-trisubstituted-azetidin-2-ones are useful organic synthons for the synthesis of various heterocyclic compounds having diverse pharmacological applications.
Keywords: Lactams, oxa-michael reaction, 3-hydroxy lactams, acetylenic ester, pharmacological applications, organic synthesis.
Graphical Abstract
[http://dx.doi.org/10.1021/cr0684016] [PMID: 18072803]
[http://dx.doi.org/10.1055/s-2007-966005]
[http://dx.doi.org/10.1021/jo00097a039]
[http://dx.doi.org/10.1016/S0040-4020(02)00991-2]
[http://dx.doi.org/10.1039/p19910002435]
[http://dx.doi.org/10.1039/CS9962500117]
[http://dx.doi.org/10.1021/ja960766s]
[http://dx.doi.org/10.1016/S0957-4166(97)00534-X]
[http://dx.doi.org/10.1002/chem.200902236] [PMID: 19798719]
[http://dx.doi.org/10.1080/00304940509354981]
[http://dx.doi.org/10.1021/ol5022178] [PMID: 25144533]
[http://dx.doi.org/10.1021/jo902634a] [PMID: 20180509]
[http://dx.doi.org/10.1002/ejoc.200500593]
[http://dx.doi.org/10.1039/b718357g] [PMID: 18497934]
[http://dx.doi.org/10.1039/C1CS15167C] [PMID: 21796323]
[http://dx.doi.org/10.1021/ol100431m] [PMID: 20222688]
(b) Zhang, X.; Zhang, S.; Wang, W. Angew. Chem. Int. Ed., 2010, 49, 1481.
[http://dx.doi.org/10.1002/anie.200906050]
[http://dx.doi.org/10.1021/jm201344a] [PMID: 22329561]
[http://dx.doi.org/10.1016/j.bmc.2006.12.031] [PMID: 17234419]
[http://dx.doi.org/10.1016/j.ejmech.2010.09.035] [PMID: 20970895]
[http://dx.doi.org/10.1016/j.bmcl.2008.09.064] [PMID: 18835165]
[http://dx.doi.org/10.1016/S0960-894X(01)80714-9]
[http://dx.doi.org/10.1039/C6RA20973D]
[http://dx.doi.org/10.1016/j.tetlet.2010.06.038]
[http://dx.doi.org/10.1016/j.ejmech.2012.10.049] [PMID: 23164657]
[http://dx.doi.org/10.1016/j.tetlet.2014.02.105]
[http://dx.doi.org/10.1055/s-0034-1379734]
[http://dx.doi.org/10.1039/C6RA10021J]
[http://dx.doi.org/10.24820/ark.5550190.p009.845]
[http://dx.doi.org/10.1021/jo991641j] [PMID: 10843611]
(b) Alcaide, B.; Almendros, P.; Campo, T.M.D.; Acebesa, R.R. Adv. Synth. Catal., 2007, 349, 749.
[http://dx.doi.org/10.1002/adsc.200600502]
[http://dx.doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3223:AID-EJOC3223>3.0.CO;2-1]
[http://dx.doi.org/10.1016/S0040-4020(01)88276-4]