《aconvenientsynthesisofphosphonomethylα,β-unsaturatedγ-lactams.》

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1、TetrahedronLetters56(2015)5397–5400ContentslistsavailableatScienceDirectTetrahedronLettersjournalhomepage:www.elsevier.com/locate/tetletAconvenientsynthesisofphosphonomethyla,b-unsaturatedc-lactamsa,baba,⇑b,⇑AbderrahmenAbdelli,MohamedLotfiEfrit,AnneGaucher,HediM’rabet,DamienPrimaUn

2、iversitédeTunisElManar,FacultédesSciencesdeTunis,LaboratoiredeSynthèseOrganiqueetHétérocyclique,2092Tunis,TunisiabUniversitédeVersaillesSaintQuentin-en-Yvelines,InstitutLavoisierdeVersailles-UMRCNRS8180,45avenuedesEtats-Unis,78035Versailles,FrancearticleinfoabstractArticlehistory:

3、Aversatileaccesstodiverselysubstituteda,b-unsaturatedc-lactamsisdescribedusingacommonReceived6July2015allylphosphonateprecursor.Theconstructionofthec-lactammotiveisbasedontwostepsincludingaRevised28July2015keysequentialone-potMichaeladdition–Nefsequencethatallowsthepreparationofke

4、to-esterinterme-Accepted31July2015diates.Ourmethodologyallowedtheselectiveinstallationofvariousalkyl,cycloalkylandarylsub-Availableonline3August2015stituentsaswellasavaluablephosphonomethylfragmentatpositions1and3oftheheterocycle.Ó2015ElsevierLtd.Allrightsreserved.Keywords:Keto-es

5、tersc-LactamsAllylphosphonatesMichaeladditionNefreactionIntroductiondihydropyrrol-2-onederivatives(Fig.2).Ourstrategyisbasedontheconstructionofthec-lactamscaffoldfromc-ketoesterinter-a,b-Unsaturatedc-lactamsalsocalleddihydropyrrol-2-onesmediatesobtainedfromallylphosphonatesaskeypr

6、ecursors.representasubclassofthemoregeneralc-lactamfamily.ThewideWefirststartedtoexaminethetransformationofallylphospho-panelofpharmaceuticalandbiologicalactivitiesdisplayedbysuchnatesintoc-ketoesters.Atafirstglance,weenvisionedtwoinde-1aza-heterocyclesfocusedtheinterestofthescienti

7、ficcommunity.pendentstepsimplyingfirstMichaeltypeadditionofaliphatic211SelectedexamplesdepictedinFigure1,showherbicidal1andnitrocompoundstotheallylgroupfollowedbyaNefreaction3antitumor2activitiesaswellasantibacterialandcytotoxicprop-toaffordtheexpectedphosphonomethylc-ketoesters.4er

8、ties5(Fig.1).Theheterocyclicpatte