green,efficent and practical michael addition of arylamines to α,β-unsaturated ketones

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1、Tetrahedron67(2011)3631e3637ContentslistsavailableatScienceDirectTetrahedronjournalhomepage:www.elsevier.com/locate/tetGreen,efficientandpracticalMichaeladditionofarylaminestoa,b-unsaturatedketonesRanJiang,Dan-HuaLi,JingJiang,Xiao-PingXu*,TaoChen,Shun-JunJi*KeyLaboratoryofOrganicSynthesisofJiang

2、suProvince,CollegeofChemistry,ChemicalEngineeringandMaterialsScience,SoochowUniversity,Suzhou215123,ChinaarticleinfoabstractArticlehistory:Theaza-Michaeladditionofaromaticaminestoa,b-unsaturatedketoneswascarriedouteffectivelyatReceived5March2011roomtemperatureingoodtoexcellentyieldswithoutanyca

3、talystorsolvent.ItwassignificantthatpartReceivedinrevisedform21March2011ofadductscouldbecollectedinalmostquantitativeyieldwithoutcolumnchromatography.Thispro-Accepted25March2011cedureofferedagreen,efficient,andpracticalapproachforthesynthesisofb-aminoketones.Availableonline31March2011Ó2011Elsevie

4、rLtd.Allrightsreserved.Keywords:Michaeladditionb-AminoketonesSolvent-freeCatalyst-free1.Introductioncatalystorsolventwasrequiredinthesereactions,thearomaticaminesweredemonstratedtobealmostinertinthereactionpos-Theb-aminocarbonylmoietyisalwaysfoundinbiologicalsiblyasaresultoftheirweakernucleophi

5、licity.4,12,13,14bOntheproductsandpharmaceuticallyactivesubstances.1Overthepastotherhand,theselectivityofmono-additionanddi-additionwasdecades,manyapproacheshavebeendevelopedforthesynthesischallengeincatalyticsystems.Inourcontinuingeffortstodevelopofthisskeleton.Amongthesemethods,theaza-Michael

6、additionisgreenproceduresforthe1,4-conjugatedaddition,18wehereinpreferableduetoitsatomeconomy,highselectivity,andsimplediscloseanefficientapproachforthemono-additionofaromaticprocesses.Agreatdealofcatalystsystemshavebeenexploredtoaminestoa,b-unsaturatedketoneswithhighselectivity,whichdateforthet

7、ransformation2usingLewisacids(In,3Yb,4Cu,5Bi,6performsatroomtemperatureinabsenceofanycatalystorsolventFe,7Sm,8molecularIodine,9Pd,10etc.),Brønstedacids,11base,12(Scheme1).Inaddition,themostoften-usedpurificationmethodsionicliquid,1