喹啉羧酸及其衍生物的合成方法-黄文静

doi10．16597/j．cnki．issn．1002－154x．2016．01．009*****222005*221116、。。2016－01－11201305007、YY－026SW－YY－028CG1302CG15081993～。1964～。[e-mail]neCarboxylicAcidanditsDerivativesHuangWenjingTanChaolanZhangDandanWangＲunnanZhangZhenming*WangXuan*SchoolofChemicalEngineering＆TechnologyHuaihaiInstituteofTechnologyJiangsuLianyungang222005*SchoolofChemicalEngineering＆TechnologyChinaUniversityofMiningandTechnologyJiangsuXuzhou221116AbstractQuinolinecarboxylicAcidanditsderivativeswereimportantintermediatesinorganicsynthesiswhichwerewidelyusedinpharmaceuticalagriculturalchemicalsanddyeindustries．Themainsynthesismethodsofquinol-inecarboxylicacidanditsderivativesincludingdirectoxidationhydrolysiscyclizationandothersyntheticmethodwerereviewed．KeywordsquinolinecarboxylicacidOxidationCyclization。、3－－－2－－4－1VLA－4、urotensinⅡ、、－2－4－－3－223－。－2－2－－8－－－7－3－6－4Hqlc。。。1、、Ｒessert—33—30120161ChemicalIndustryTimesVol．30No．1Jan．1．20161。1Fig1synthesismethodsofquinolinecarboxylicacid1．12～7、、、。、SakaguchiS5N－2～75。2．22－2－2－695%。2．3Ｒessert、Ｒessert2－54%2。2．4Friedlnder、Skraup、Pfitz-ingerNiementowski。Friedlnderα－23－。Skraup、5678－。Pfitzinger4－24－。Niementowski、。2。23456782324。2．1－2－Ｒessert。7－Friedlnder2－。Huang8－2－80%。Ge9NájeraHeck2－—43—2016.Vol.30No．1《Ｒeviews》－－3－87%。4－1067。3－4－－3－。EMME。LewisPPA、PPE、Ac2O－H2SO4。。17、、。、2－－－4－651%。11Pfitzinger2－－4－94%。Matsumura125－－8－8－－5－。。6－SkraupMcCall13、、－6－95%。Nycz142－－8－－Kolbe－Schmidt2－－8－－7－59%。8－153－－2－Skraup7－－8－－37－－8－。、78%。2．2。23－24－。Maulding16N－－3－－3－Vilsmeier23－54%。LosM17β－－αβ—53—2016.Vol.20No．1Vilsmeier23－74%。1823－23－85．3%。Zhu1924－90%。Nan2024－75%。3。Skraup6857。575。Friedlnder。PfitzingerFriedlnder。。1PendrakIWittrockＲKingsburyWD．Synthesisandan-ti－HSVactivityofmethylenedioxymappicineketoneana-logsJ．J．Org．Chem．19956092912～2915．2．4－J．201406785～790．3MaleckiJGKruszyńskiＲTabakD．etal．Thereac-tionsbetweenＲuHClCOPPh33andquinolinecar-boxylicacidsJ．Polyhedron200726175120～5130．4XuBGuoZYangH．etal．AnovelluminescentLeadcoordinationframeworkwithquinoline－6－carboxylicacidJ．JournalofMolecularStructure20099221140～143．5SakaguchiSShibamotoAIshiiY．Ｒemarkableeffectof—63—2016.Vol.30No．1《Ｒeviews》nitrogendioxideforN－hydroxyphthalimide－catalyzedaerobicoxidationofmethylquinolinesJ．ChemicalCom-munications20022180～181．6FurnissBS．Vogel＇stextbookofpracticalorganicchemistryM．PearsonEducationIndia1989．7．2D．2010．8HeHuangHualiangJiangKaixianChenandHongLiu．ASimpleandConvenientCopper－CatalyzedTandemSynthe-sisofQuinoline－2－carboxylatesatＲoomTemperature．J．Org．Chem．200974155476～5480．9GeDHuLWangJ．ＲeversibleHydrogenationOxida-tiveDehydrogenationofQuinolinesoveraHighlyActivePtNanowireCatalystunderMildConditionsJ．Chem-CatChem2013582183～2186．10．6－－7－－4－－3－J．200905694～698．11．－4－J．201356281～282．12MatsumuraKSoneC．TheBeckmannＲearrangementwithQuinolineCompoundsJ．JournaloftheAmericanChemicalSociety19315341493～1496．13McCallJMＲomeroDLClareM．Heterocycliccom-poundsfortheinhibitionofpaskP．US20121491572012－3－2．14NyczJEMaleckiGJ．Synthesisspectroscopyandcom-putationalstudiesofselectedhydroxyquinolinecarboxylicacidsandtheirselectedfluoro－thio－anddithioana-loguesJ．JournalofMolecularStructure20131032159～168．15．J．199635617～18．16MauldingDＲ．Synthesisof23－quinolinedicarboxylicacidJ．Journalofheterocyclicchemistry19882561777～1779．17LosM．2－2－imidazolin－2－yl－pyridinesandquinolinesanduseofsaidcompoundsasherbicidala-gentsU．S．Patent4798619P．1989－1－17．18．3－P．CN101781247B2013－01－02．19ZhuHYangＲFYunLH．etal．Facileandefficientsynthesisofquinoline－4－carboxylicacidsundermicro-waveirradiationJ．ChineseChemicalLetters201021135～38．20NanGMLiuW．Metal－freeone－potsynthesisofquinoline－24－carboxylatesviaamoleculariodine－catalyzedthree－componentreactionofarylaminesethylglyoxylateandα－ketoestersJ．ChineseChemicalLetters20152610檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸檸1289～1292．。。。“”2015“”。。。、、、、、。“、、、、”。GMP、、。—73—2016.Vol.20No．1