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1、SubscriberaccessprovidedbyTSINGHUAUNIVNoteAConvenientandHighlyRegioselectiveOne-PotSynthesisofQuinolinesbyAdditionofaVilsmeier-TypeReagenttoN-AryliminesAlanR.Katritzky,andMichaelArendJ.Org.Chem.,1998,63(26),9989-9991•DOI:10.1021/jo981252+•PublicationDate(Web):25November1998Downloadedf
2、romhttp://pubs.acs.orgonFebruary26,2009MoreAboutThisArticleAdditionalresourcesandfeaturesassociatedwiththisarticleareavailablewithintheHTMLversion:•SupportingInformation•Linkstothe1articlesthatcitethisarticle,asofthetimeofthisarticledownload•Accesstohighresolutionfigures•Linkstoarticl
3、esandcontentrelatedtothisarticle•Copyrightpermissiontoreproducefiguresand/ortextfromthisarticleTheJournalofOrganicChemistryispublishedbytheAmericanChemicalSociety.1155SixteenthStreetN.W.,Washington,DC20036J.Org.Chem.1998,63,9989-99919989AConvenientandHighlyRegioselectiveScheme1One-Pot
4、SynthesisofQuinolinesbyAdditionofaVilsmeier-TypeReagenttoN-AryliminesAlanR.Katritzky*andMichaelArendCenterforHeterocyclicCompounds,DepartmentofChemistry,UniversityofFlorida,Gainesville,Florida32611-7200ReceivedJune29,1998Quinolinesandtheirderivativesoccurinnumerousnaturalproducts.1Man
5、yquinolinesdisplayinterestingphysiologicalactivitiesandhavefoundattractiveap-plicationsaspharmaceuticals(e.g.,antimalarialdrugssuchasquinineorchloroquine)andagrochemicalsaswellasbeinggeneralsyntheticbuildingblocks.1bManyDMF,andSOCl.7Salt2actsasastablesyntheticsyntheseshavebeendevelope
6、dforquinolines,2butdue2chloroiminiumsalt[ClCHdNMe2]+X-equivalent(i.e.,thetotheirgreatimportance,thedevelopmentofnovel3benzotriazolemoietyiseasilysubstitutedbynucleo-syntheticmethodsremainsanactiveresearcharea.philes),and2canbehandledwithoutspecialprecautions.Theknownsynthesesofquinoli
7、nesfromenaminesandInaddition,theuseof2allowsmildreactionconditionsVilsmeierreagentseitherrequirealargeexcessofPOCl3andacleanworkup.(orPOCl3asasolvent)orareoflimitedscope(e.g.,ExperimentsmonitoredbyNMRspectroscopyindi-reactionsoftertiaryenaminesandN-arylVilsmeiercatedthatN-arylimines1r
8、eactw
