合成路线:The condensation of 3,5-dimethylisoxazole (I) with ethylene oxide (II) by means of butyllithium in THF gives 3-(3-methylisoxazol-5-yl)-1-propanol (III),which by reaction with refluxing SOCl2 yields the corresponding propyl chloride (IV).The condensation of (IV) with 4-hydroxy-3,5-dimethylbenzonitrile (V) [obtained by reaction of 4-bromo-2,6-dimethylphenol (VI) with Cu2CN2 in refluxing DMF] by means of K2CO3 and KI in hot N-methylpyrrolidone affords 3,5-dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy]benzonitrile (VII).The reaction of (VII) with hydroxylamine (VIII) and K2CO3 in refluxing ethanol gives the corresponding benzohydroxamic acid (IX),which is finally cyclized with refluxing trifluoroacetic anhydride and pyridine.
参考文献标题:1,2,4-Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
文献作者:Diana,G.D.; Nitz,T.J.(Sanofi-Synthabo)
参考来源:US 5464848
合成路线:The condensation of 3,5-dimethylisoxazole (I) with ethylene oxide (II) by means of butyllithium in THF gives 3-(3-methylisoxazol-5-yl)-1-propanol (III),which by reaction with refluxing SOCl2 yields the corresponding propyl chloride (IV).The condensation of (IV) with 4-hydroxy-3,5-dimethylbenzonitrile (V) [obtained by reaction of 4-bromo-2,6-dimethylphenol (VI) with Cu2CN2 in refluxing DMF] by means of K2CO3 and KI in hot N-methylpyrrolidone affords 3,5-dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy]benzonitrile (VII).The reaction of (VII) with hydroxylamine (VIII) and K2CO3 in refluxing ethanol gives the corresponding benzohydroxamic acid (IX),which is finally cyclized with refluxing trifluoroacetic anhydride and pyridine.
参考文献标题:VP-63843
文献作者:Fromtling,R.A.; Castar,J.
参考来源:Drugs Fut 1997,22(1),40
合成路线:The condensation of 3,5-dimethylisoxazole (I) with ethylene oxide (II) by means of butyllithium in THF gives 3-(3-methylisoxazol-5-yl)-1-propanol (III),which by reaction with refluxing SOCl2 yields the corresponding propyl chloride (IV).The condensation of (IV) with 4-hydroxy-3,5-dimethylbenzonitrile (V) [obtained by reaction of 4-bromo-2,6-dimethylphenol (VI) with Cu2CN2 in refluxing DMF] by means of K2CO3 and KI in hot N-methylpyrrolidone affords 3,5-dimethyl-4-[3-(3-methylisoxazol-5-yl)propoxy]benzonitrile (VII).The reaction of (VII) with hydroxylamine (VIII) and K2CO3 in refluxing ethanol gives the corresponding benzohydroxamic acid (IX),which is finally cyclized with refluxing trifluoroacetic anhydride and pyridine.
参考文献标题:Picornavirus inhibitors: Trifluoromethyl substitution provides a global protective effect against hepatic metabolism
文献作者:Pevear,D.C.; Rudewicz,P.; Diana,G.D.; Nitz,T.J.; Aldous,S.C.; Aldous,D.J.; Robinson,D.T.; Draper,T.; Dutko,F.J.; Aldi,C.; et al.
参考来源:J Med Chem 1995,381355-71
产品链接: CAS No. 153168-05-9››