有机叠氮化合物的合成与应用进展__有机叠氮化合物的合成方法_王莉莉

,2010,18(1):7275SCIENCE&TECHNOLOGYINCHEMICALINDUSTRY:2009209215:(1985-),,,,333:(2002ZY120)3.1,133,2(1.,650224;2.,650224):9,,/(),:;;;;;:O622.6:A:100820511(2010)01200722041864PeterGrie,,1,2,1,21,3,,,,,Staudingerligation,,AIDS,,,,(GAP),,,;,HIV21,,,1,,(1),;(2),(N):NC+NONN3(1),,g;(3)NC/NN3,20g;NC/NN31,,,(1mol/L,5g);NC/NN1,,,1g,CH3N3;(4),,,(1);(5)(),;(6),,HN3(HCN)2,5,(1)N3();(2)N2();(3)N();(4);(5)92.1,,/GAP()(PECH)3PECH,GAP,PECH,(ATGAP),;JayakrishnanSunny[1][2],27%2.2(1),Monica[3],,77%(2),LewisZn(N3)22Py,(PPh3)2,4,4,6222,52,[4][H2NMP]HSO4,N,N2(DMF),;Sampach[5],BF3Et2O,35h80%2.3,Nitin[6],,87%,Lavinia[7],,76%93%,,;Subhas[8]0,(95%),Curtius2.4,,,,,()(1),:Gumaste[9],,Curtius,95%,;,;Tale[10]3,4,52,3,4,52(2)Liu[11],,371,.;(3)Shao[12](DPPA),Cyrous[13](22),90%,,2.5,,,Bohumil[14]52242,,,,,2.6,HN3,[15],HN3,99%;,Ali2Reza[16],,2.7/NaN3Mao[17],,80%82,CuSO4,[18],2.8,,,,,,,;42,42,TiO2,PP[17]2.9,,3,[19]2.109,,Mit2sunobu,Stefan[20][][1]JAYAKRISHNANA,SUNNYMC.Phasetransfercatal2ysedsurfacemodificationofplasticizedpoly(vinylchloride)inaqueousmediatoretardplasticizermigrateon[J].Poly2mer,1996,37(23):52135218.[2]JAYAKRISHNANA,SUNNYMC,MiniNRajan.Pho2tocrossingofazidatedpoly(vinylchloride)coatedontoplas2ticizedPVCsurface:routetocontainingplasticizermigration[J].JournalofAppliedPolymerScience,1995,56:11871195.[3]MonicaCatasus,AgustiBueno,AlbertMoyano,etal.2Fer2rocenyl22aminoalcohols:anewclassofcentralchiralferro2cenederivateives[J].JournalofOrganometallicChemistry,2002,642:212226.[4]Akikosaito,Kazumisaito,AkiraTanaka,etal.Anefficientmethodforconvertingalcoholstoazideswith2,4,4,62tet2rabromo22,52cyclohexadienone/PPh3/Zn(N3)22Py[J].TetrahedronLetters,1997,38(22):39553958.[5]SAMPETHKUMARHM,SUBBAREDDYBV,AN2JANEYULUS,etal.Anexpedientandhighlyselectiveconver2sionofalcoholstoazidesusingaNaN3/BF3Et2Osystem[J].TetrahedronLetters,1998,39(40):73857388.[6]NitinDArote,KrishnacharyaGAkamanchi.Directconversion4718ofaldehydestoacylazidesusingtert2butylhypochlorite[J].Tet2rahedronLetters,2007,48(32):56615664.[7]LaviniaGeorgetaMarinescu,ChristianMarcusPedersen,MikaelBols.Saferadicalazidonationusingpolystyrenesupporteddiaz2idoiodate(I)[J].Tetrahedron,2005,61:123127.[8]SUBHASBOSED,NARSIMHAREDDYAV.Iodine(V)reagentsinorganicsynthesis.Dess2Martinperiodinaneme2diatedefficientone2potoxidationofaldehydestoacylazides[J].TetrahedronLetters,2003,44(17):35433545.[9]GUMASTECVK,BHAWALBM,DESHMUKHARAS.Amildandefficientmethodforthepreparationofacylazidesfromcarboxylicacidsusingtriphosgene[J].Tetra2hedronLetters,2002,43(7):13451346.[10]TALERH,PATILKMPatil.3,4,52Trifluorobenzenebo2ronicacid:amildandversatilecatalystfortheone2potsyn2thesisofacylazidesfromcarboxylicacids[J].TetrahedronLetters,2002,43(52):97159716.[11]LiuRX,ZhangBW,TangHX.Synthesisandcharacteriza2tionofpoly(acrylaminophosphonic2carboxyl2hydrazide)chelatingfibre[J].ReactiveandFunctionalPolymers,1999,39:7181.[12]SHAOHui,MarcusColucci,TONGShao2jing,etal.Aprac2ticalsolidphasesynthesisofquinazoline22,42diones[J].TetrahedronLetters,1998,39(40):72357238.[13]CyrousOKangani,BillyWDay,DavidEKelley.Direct,fac2ilesynthesisofacylazidesandnitrilesfromcarboxylicacidsusingbis(22methoxyethyl)aminosulfurtrifluoride[J].Tet2rahedronLetters,2007,48(34):59335937.[14]BohumilDolensky,YoshioTakeuchi,LouisACohen,etal.Synthesisof4,52difluoroimidazole[J].JournalofFluorineChemistry,2001,107(1):147148.[15]CHENShu2wei,SantoshSinghThakur,LIWen2ji,etal.Ef2ficientcatalyticsynthesisofopticallypure1,22azidoalco2holsthroughenantioselectiveepoxideringopeningwithHN3[J].JournalofMolecularCatalysisA:Chemical,2006,259(12):116120.[16]Ali2RezaKiasat,MaryamZayadi.Polyethyleneglycolimmo2bilizedonsilicagelasanewsolid2liquidphase2transfercata2lystforregioselectiveazidolysisofepoxidesinwater:Anef2ficientrouteto1,22azidoalcohols[J].CatalysisCommunica2tions,2008,9(10):20632067.[17]MAOChun,ZHANGCan,QIUYong2zhi,etal.Introduc2tionofanticoagulationgrouptopolypropylenefilmbyradia2tiongraftinganditsbloodcompatibility[J].AppliedSurfaceScience,2004,228(14):2633.[18]LIUQ,TORY.Simpleconversionofaromaticaminesintoazides[J].OrgLett,2003,5:25712572.[19]YADAVJS,SUBBAREDDYBV,TapasMaity,etal.Adiastereoselectivesynthesisof42azidotetrahydropyransviatheprins2cyclization[J].TetrahedronLetters,2007,48(40):71557159.[20]STEFANB,GARMENG,KERSTINK,etal.Organicaz2ides:anexplodingdiversityofauniqueclassofcompounds[J].AngewandteChemie,2005,44(33):51885240.Advanceonthesynthesisandapplicationoforganicazides.ThesyntheticmethodsoforganicazidesWANGLi2li1,TANGHui1,ZHANGXiao2chun2(1.FacultyofChemicalEngineering,KunmingUniversityofScienceandTechnology,Kun2ming650224,China;2.FacultyofModernAgriculturalEngineering,KunmingUniversityofSci2enceandTechnology,Kunming650224,China)Abstract:Inpresentpaper,thesyntheticmethodsoforganicazidesanditsapplicationinresentyearswerereviewed.Saftyprecautionandnineofmethodsforthesynthesisoforganicazideswereintro2duced,includingsubstitutionreactionofhalidebyazidationreagent,azidationofaldehyde,carboxylicacid,ester,alcohol,epoxides,aromaticamines/heterocyclic(aromati