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1、PRACTICALSYNTHETICPROCEDURES1053MildandHigh-YieldingSynthesisofb-KetoEstersandb-KetoamidesSynthesisofVellaisamySridharan,MiriamRuiz,J.CarlosMenéndez*b-KetoEstersandb-KetoamidesDepartamentodeQuímicaOrgánicayFarmacéutica,FacultaddeFarmacia,UniversidadComplutense,28040Madr
2、id,SpainFax+34(91)3941822;E-mail:josecm@farm.ucm.esReceived30June2009;revised12October2009Abstract:Inthepresenceofsodiumacetate,thereactionbetween2,2,6-trimethyl-4H-1,3-dioxin-4-oneandsecondaryortertiaryalcohols(includingchiralones)orprimaryorsecondaryaminescoul
3、dbecarriedoutinrefluxingtetrahydrofuran,undermuchmilderconditionsthanthosedescribedintheliterature.Inthesenewconditions,sideproductsnormallyobservedusingthetraditionalprotocolwereavoided,andb-ketoestersandb-ketoamideswerenormallyobtainedinquantitativeyields.Keywords:ace
4、toacetylation,chiralauxiliaries,dicarbonylcompounds,esters,amidesR1ZH(2)OOONaOAc,THF,refluxR1OO(Z=O,NH,NR2)Z31Scheme1b-Dicarbonylcompoundsarerecognizedasveryimpor-berofproblemsareassociatedwithitsuse,suchashightantbuildingblocksinorganicsynthesisandareusedforreactivitya
5、ndmoisturesensitivity,coupledtoitslachry-theconstructionofavarietyofbiologicallyrelevantmol-matoryandtoxiccharacter.Thesedrawbackspromptedecules.1TheyarealsoexcellentstartingmaterialsfortheClemensandHyatttodevelopaconvenientalternativetosynthesisofheterocycliccompoundss
6、uchasdihydropy-diketene,namely2,2,6-trimethyl-4H-1,3-dioxin-4-oneridines(Hantzsch),pyrroles(Knorr),dihydropyrimidines(1),a1:1acetone–diketeneadduct.7Pyrolysisofcom-(Biginelli),indoles(Nenitzescu),quinolines(Combes,pound1at150°Cinhigh-boilingsolventsgivesConrad–Limpach,F
7、riedländer,Knorr),oftenthroughacetylketenethrougharetro-hetero-Diels–Alderreactionmulticomponentstrategies.1b,2Furthermore,b-dicarbonylandthisintermediatecanbetrappedbynucleophilestocompoundscanalsobeusedfortheconstructionofcar-givetheiracetoacetylationproducts.Inadditi
8、ontotheob-bocyclesbymeansofC–Cbondformationreactions.3viousdisadvantagesoftherequirementforhightempera-tures,s
