Altoqualine, 458-L(non-sterochem.)
阿托喹啉 7-氨基-4,5,6-三乙氧基-3-(6,7,8-三甲氧基-2-甲基-3,4-二氢-1H-异喹啉-1-基)-3H-2-苯并呋喃-1-酮 Chemical Name: (3S)-7-Amino-4,5,6-triethoxy-3-[(1R)-1,2,3,4-tetrahydro-6,7,8-trimethoxy-2-methyl-1-isoquinolinyl]-1(3H)-isobenzofuranone
CAS No. 121029-11-6, 73604-83-8 (no stereoch)
项目整合开发状态: Preclinical
项目研究机构: Laborec (Originator)
合成路线:The formylation of 3,4,5-trimethoxyphenylethylamine (I) with formic acid - acetic anhydride gives N-formyl-3,4,5-trimethoxyphenylethylamine (II),which is cyclized in hot POCl3 to afford 6,7,8-trimethoxy-3,4-dihydroisoquinoline (III).The methylation of (III) with methyl iodide in acetone yields 2-methyl-6,7,8-trimethoxy-3,4-dihydroisoquinolinium iodide (IV),which is condensed with 4,5,6-triethoxy-7-nitrophthalide (V) by means of K2CO3 in methanol yielding 2-methyl-6,7,8-trimethoxy-1-(4,5,6-triethoxy-7-nitro-3-phthalidyl)-1,2,3,4-tetrahydroisoquinoline (VI).Finally,this compound is reduced with H2 over Raney-Ni in ethanol.
📌 参考资料/链接：
参考文献标题:458-L
文献作者:Castar,J.; Blancafort,P.; Serradell,M.N.
参考来源:Drugs Fut 1982,7(5),317
📄 详细内容
合成路线:The formylation of 3,4,5-trimethoxyphenylethylamine (I) with formic acid - acetic anhydride gives N-formyl-3,4,5-trimethoxyphenylethylamine (II),which is cyclized in hot POCl3 to afford 6,7,8-trimethoxy-3,4-dihydroisoquinoline (III).The methylation of (III) with methyl iodide in acetone yields 2-methyl-6,7,8-trimethoxy-3,4-dihydroisoquinolinium iodide (IV),which is condensed with 4,5,6-triethoxy-7-nitrophthalide (V) by means of K2CO3 in methanol yielding 2-methyl-6,7,8-trimethoxy-1-(4,5,6-triethoxy-7-nitro-3-phthalidyl)-1,2,3,4-tetrahydroisoquinoline (VI).Finally,this compound is reduced with H2 over Raney-Ni in ethanol.
参考文献标题:D閞iv閟 de phtalidyl-isoquinol閕nes,leur pr閜aration et leur application comme m閐icaments
文献作者:
参考来源:FR 2424271
产品链接: CAS No. 121029-11-6›› 产品链接: CAS No.73604-83-8››