Synthesis of 3-methoxyellipticine and ellipticine by friedel-crafts reaction of indole-2,3-dicarboxylic anhydride and selective demethylation
Synthesis of 3-methoxyellipticine and ellipticine by friedel-crafts reaction of indole-2,3-dicarboxylic anhydride and selective demethylation
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2,3-吲哚二酸酐傅克反应及选择性脱甲基合成3-甲氧基玫瑰树碱及玫瑰树碱
DOI：
10.3987/com-05-10522
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发表时间：
2005
期刊：
影响因子：
0.6
通讯作者：
H. Hibino
中科院分区：
文献类型：
--
作者：
Y. Miki*;Y. Aoki;Yasuhiko Tsuzaki;Hideaki Umemoto;H. Hibino
1-苄基吲哚-2，3-二羧酸酐与2，4，6-三甲氧基吡啶在路易斯酸存在下反应，高产率地得到唯一产物1-benzyl-3-(2，4，6-trimethoxynicotinoyl)indole-2-carboxylic酸，可转化为1-benzyl-3-(2，4，6-trimethoxynicotinoyl)indole.1-苄基-3-(2，4，6-三甲氧基烟酰基)吲哚通过甲氧基的选择性脱甲基化和三氟化制得3-甲氧基-椭圆碱和椭圆碱。
Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with 2,4,6-trimethoxypyridine in the presence of a Lewis acid gave 1-benzyl-3-(2,4,6-trimethoxynicotinoyl)indole-2-carboxylic acid as the sole product in high yield, which could be changed to 1-benzyl-3-(2,4,6-trimethoxynicotinoyl)indole. 1-Benzyl-3-(2,4,6-trimethoxynicotinoyl)indole was converted to 3-methoxy-ellipticine and ellipticine by selective demethylation and triflation of the methoxy group.