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1、S1SupportingInformationfor5-Carbonyl-1,3-oxazine-2,4-dionesfromN-CyanosulfoximinesandMeldrum’sAcidDerivatives†††‡‡FelixBrosge,JohannesFlorianKochs,MarielaBregu,Khai-NghiTruong,KariRissanen,and,†CarstenBolm†InstituteofOrganicChemistry,RWTHAachenUniversity,Landoltweg1,52074Aachen,
2、Germany‡DepartmentofChemistry,UniversityofJyvaskyla,P.O.Box35,Survontie9B,40014Jyväskylä,FinlandE-mail:Carsten.Bolm@oc.rwth-aachen.deTableofContentSectionPage1.GeneralinformationS22.Chemicalsynthesesandanalyticaldataofstartingmaterials3and8S23.Chemicalsynthesesandanalyticaldatao
3、fproducts13S64.NMRspectraS125.SingleCrystalX-raystructureof13aaS416.ReferencesS42S21.GeneralinformationUnlessotherwisestated,allreactionswerecarriedoutunderambientatmosphereandmagneticstirring.Liquidsandsolutionsweretransferredviasyringes.AnhydroussolventsweretakenfromanMBRAUNso
4、lventpurificationsystemorpurchasedfromcommercialsuppliersasextradrysolventsovermolecularsievesinsealedbottles.N-Cyanosulfoximines3andMeldrum’sacidderivatives81,2werepreparedusingconventionalproceduresknownintheliterature(section2).Allotherreagentswereobtainedfromcommercialsuppli
5、ersandusedwithoutfurtherpurification.Oilbathswereusedasheatingsourcesforallreactionsthatrequiredelevatedtemperatures.Thereactionprogresswasmonitoredbythinlayerchromatography(TLC)withaluminiumsheetssilicagel60F254fromMerckanddetectionofthecompoundswithanUVlamp(λ=254nmand365nm).Fl
6、ashcolumnchromatography(FCC)purificationswereperformedonAcrosOrganicssilicagel60A(35-70µm)usingstandardtechniques.Nuclearmagneticresonance(NMR)spectrawererecordedatroomtemperatureinCDCl3or(CD3)2SOonAgilentVNMRS600,AgilentVNMRS400,BrukerAvanceNeo400orBrukerAvance600.Chemicalshift
7、s(δ)aregiveninpartspermillion(ppm)relativetothe1131residualsolventpeaks[CDCl3:HNMRδ=7.26ppm;CNMRδ=77.16ppm;(CD3)2SO:HNMR13δ=2.50ppm;CNMRδ=39.52ppm].Couplingconstants(J)arereportedinHz.Multiplicitiesareabbreviatedbys(singlet),d(doublet),dd(doubletofdoublet),t(triplet),tt(tripleto
8、ftriplet),q(quartet),br(broad)andm(multiplet).M
