Spizofurone, AG-629, Maon
螺佐呋酮Chemical Name: 5-Acetylspiro[benzofuran-2(3H),1'-cyclopropan]-3-one
CAS No. 72492-12-7
项目整合开发状态: Withdrawn-1988
项目研究机构: Takeda (Originator)
合成路线:The reaction of methyl-5-acetylsalicylate (I) with alpha-bromo-gamma-butyrolactone (II) by means of K2CO3 in refluxing acetone gives alpha-[(2-methoxycarbonyl-4-acetylphenyl)oxy]-gamma-butyrolactone (III),which is hydrolyzed with NaOH in methanol yielding alpha-[(2-carboxy-4-acetylphenyl)oxy]-gamma-butyrolactone (IV).The cyclization of (IV) with refluxing acetic anhydride affords 5-acetyl-4',5'-dihydrospiro[benzofuran-2(3H),3'(2'H)-furan]-2',3-dione (V),which is finally treated at 155 C in dimethylsulfoxide containing NaCl.
📌 参考资料/链接：
参考文献标题:Spirobenzofuranone compounds,processes for their preparation and their use as medicines
文献作者:Hirosada,S.; Watanabe,M.; Mitsuru,K.; Isuke,I.(Takeda Chemical Industries,Ltd.)
参考来源:CA 1113467; DE 2861651; EP 0003084; ES 476330; ES 8102114; JP 54098752; ZA 7807296
📄 详细内容
合成路线:The reaction of methyl-5-acetylsalicylate (I) with alpha-bromo-gamma-butyrolactone (II) by means of K2CO3 in refluxing acetone gives alpha-[(2-methoxycarbonyl-4-acetylphenyl)oxy]-gamma-butyrolactone (III),which is hydrolyzed with NaOH in methanol yielding alpha-[(2-carboxy-4-acetylphenyl)oxy]-gamma-butyrolactone (IV).The cyclization of (IV) with refluxing acetic anhydride affords 5-acetyl-4',5'-dihydrospiro[benzofuran-2(3H),3'(2'H)-furan]-2',3-dione (V),which is finally treated at 155 C in dimethylsulfoxide containing NaCl.
参考文献标题:AG-629
文献作者:Blancafort,P.; Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1983,8(2),92
产品链接: CAS No. 72492-12-7››