合成路线:Deoxybenzoin (I) is converted to the corresponding oxime (II) by treatment with NH2OH稨Cl under basic conditions either with sodium acetate in aqueous ethanol or in toluene in presence of potassium hydroxide in absolute ethanol.Deprotonation of the oxime under nitrogen with 2eq of butyllithium in THF followed by cyclization in ethyl acetate or acetic anhydride affords isoxazoline (III).Finally,treatment of (III) with cold chlorosulfonic acid followed by reaction of the intermediate sulfonyl chloride with aqueous ammonia affords the desired product.
参考文献标题:Substd.sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors
文献作者:Talley,J.J.; Sikorski,J.A.; Devadas,B.; Graneto,M.J.; Carter,J.S.; Norman,B.H.; Lu,H.-F.; Brown,D.L.(Pharmacia Corp.)
参考来源:EP 0828736; EP 0995747; US 5643933; WO 9638442
合成路线:Deoxybenzoin (I) is converted to the corresponding oxime (II) by treatment with NH2OH稨Cl under basic conditions either with sodium acetate in aqueous ethanol or in toluene in presence of potassium hydroxide in absolute ethanol.Deprotonation of the oxime under nitrogen with 2eq of butyllithium in THF followed by cyclization in ethyl acetate or acetic anhydride affords isoxazoline (III).Finally,treatment of (III) with cold chlorosulfonic acid followed by reaction of the intermediate sulfonyl chloride with aqueous ammonia affords the desired product.
参考文献标题:Isoxazole cpds.as cyclooxygenase inhibitors
文献作者:Talley,J.J.(Pharmacia Corp.)
参考来源:US 5859257
合成路线:Deoxybenzoin (I) is converted to the corresponding oxime (II) by treatment with NH2OH稨Cl under basic conditions either with sodium acetate in aqueous ethanol or in toluene in presence of potassium hydroxide in absolute ethanol.Deprotonation of the oxime under nitrogen with 2eq of butyllithium in THF followed by cyclization in ethyl acetate or acetic anhydride affords isoxazoline (III).Finally,treatment of (III) with cold chlorosulfonic acid followed by reaction of the intermediate sulfonyl chloride with aqueous ammonia affords the desired product.
参考文献标题:4-[5-Methyl-3-phenylisoxazol]4-yl]-benzenesulfonamide,valdecoxib: A potent and selective inhibitor of COX-2
文献作者:Talley,J.J.; Brown,D.L.; Carter,J.S.; Graneto,M.J.; Koboldt,C.M.; Masferrer,J.L.; Perkins,W.E.; Rogers,R.S.; Shaffer,A.F.; Zhang,Y.Y.; Zweifel,B.S.; Seibert,K.
参考来源:J Med Chem 2000,43(5),775
合成路线:Deoxybenzoin (I) is converted to the corresponding oxime (II) by treatment with NH2OH稨Cl under basic conditions either with sodium acetate in aqueous ethanol or in toluene in presence of potassium hydroxide in absolute ethanol.Deprotonation of the oxime under nitrogen with 2eq of butyllithium in THF followed by cyclization in ethyl acetate or acetic anhydride affords isoxazoline (III).Finally,treatment of (III) with cold chlorosulfonic acid followed by reaction of the intermediate sulfonyl chloride with aqueous ammonia affords the desired product.
合成路线:The acylation of 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide,valdecoxib (I),with propionic anhydride (II) by means of TEA and DMAP in THF gives N-[4-(5-methyl-3-phenylisoxazol-4-yl)phenylsulfonyl]propionamide (III),which is then treated with NaOH in ethanol.
参考文献标题:Valdecoxib and Parecoxib Sodium
文献作者:Leeson,P.; Castar,J.; Castar,R.M.; Sorbera,L.A.
参考来源:Drugs Fut 2001,26(2),133
产品链接: CAS No. 181695-72-7››