Scheme1.Synthesesofaulosirazole,pronqodineAandvariousanalogues.Reagentsandconditions:a)nBuLi,Et2O,hexanes,¢258C,18h;
dimethyldisulfide,THF,RT,4.5h,50%;b)conc.HCl,THF,RT,1.5h,82%;c)NH2OH·HCl,NaOH,EtOH,H2O,RT,20h,79%;d)sulfuryl
chloride,PhCl,RT,8088C,1h;dimethylsulfate,K2CO3,DMF,RT,16h,18%;e)Br2,AcOH,RT,1.5h,49%;f)CAN,H2O,MeCN,RT,1h,59%;
g)CAN,H2O,MeCN,RT,45h,61%;(h)pyrone8,NEt3,CHCl3,RT,40min,13%;i)pyrone8,NEt3,CHCl3,RT,15min,50%;j)conc.HCl,THF,
RT,1.5h,82%;k)NH2OH·HCl,formicacid,10088C,1.5h,63%;l)Br2,CHCl3,RT,3h,66%;m)CAN,H2O,MeCN,RT,1h,59%;n)CAN,H2O,
MeCN,RT,1h,82%;o)pyrone8,NEt3,CH2Cl2,RT,14h,30%;p)pyrone8,NEt3,CHCl3,RT,30min,30%;q)MeNH2,CeCl3·7H2O,EtOH,RT,
1h,42%;r)benzylamine,CeCl3·7H2O,EtOH,RT,30min,38%;s)pyrrolidine,CeCl3·7H2O,EtOH,RT,30min,60%.CAN=cerium(IV)
ammoniumnitrate.
Scheme1.Synthesesofaulosirazole,pronqodineAandvariousanalogues.Reagentsandconditions:a)nBuLi,Et2O,hexanes,¢258C,18h;dimethyldisulfide,THF,RT,4.5h,50%;b)conc.HCl,THF,RT,1.5h,82%;c)NH2OH·HCl,NaOH,EtOH,H2O,RT,20h,79%;d)sulfurylchloride,PhCl,RT,8088C,1h;dimethylsulfate,K2CO3,DMF,RT,16h,18%;e)Br2,AcOH,RT,1.5h,49%;f)CAN,H2O,MeCN,RT,1h,59%;g)CAN,H2O,MeCN,RT,45h,61%;(h)pyrone8,NEt3,CHCl3,RT,40min,13%;i)pyrone8,NEt3,CHCl3,RT,15min,50%;j)conc.HCl,THF,RT,1.5h,82%;k)NH2OH·HCl,formicacid,10088C,1.5h,63%;l)Br2,CHCl3,RT,3h,66%;m)CAN,H2O,MeCN,RT,1h,59%;n)CAN,H2O,MeCN,RT,1h,82%;o)pyrone8,NEt3,CH2Cl2,RT,14h,30%;p)pyrone8,NEt3,CHCl3,RT,30min,30%;q)MeNH2,CeCl3·7H2O,EtOH,RT,1h,42%;r)benzylamine,CeCl3·7H2O,EtOH,RT,30min,38%;s)pyrrolidine,CeCl3·7H2O,EtOH,RT,30min,60%.CAN=cerium(IV)ammoniumnitrate.
正在翻譯中..
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