Indoprofen类似物的合成和表征  

Synthesis and Elucidation of Indoprofen Analogues

作　　者：王思宏[1] 赵华[2] 高永俊[2] 

机构地区：[1]延边大学分析测试中心,延吉133002 [2]延边大学化学系,延吉133002

出　　处：《有机化学》2003年第9期1022-1025,共4页Chinese Journal of Organic Chemistry

摘　　要：以邻硝基苯甲醛为起始原料 ,合成 2 溴甲基 3 喹啉酸乙酯中间体 ,其分别与苯胺、2 氯代苯胺、3 氯代苯胺、2 甲基苯胺和 3 甲基苯胺发生Williamson反应 ,Williamson反应产物经闭环反应 ,得到新化合物 2 ,3 二氢 1 氧代 2 苯基 1H 吡咯并[3,4 b]喹啉 (4a) ,2 ,3 二氢 1 氧代 2 (2 氯代苯基 ) 1H 吡咯并 [3,4 b]喹啉 (4b) ,2 ,3 二氢 1 氧代 2 (3 氯代苯基 ) 1H 吡咯并 [3,4 b]喹啉 (4c) ,2 ,3 二氢 1 氧代 2 (2 甲基苯基 ) 1H 吡咯并 [3,4 b]喹啉 (4d)和 2 ,3 二氢 1 氧代 2 (3 甲基苯基 ) 1H 吡咯并 [3,4 b]喹啉 (4e) .12个新化合物由元素分析、红外光谱、核磁共振氢谱、质谱予以证实 .The Indoprofen analogues, including 2,3-dihydro-1-oxo-2-phenyl-1H-pyrrolo[3,4-b]quinoline (4a) and its congeners 2,3-dihydro-1-oxo-2-(2-chloropheny)-1H-pyrrolo[3,4-b]quinoline (4b), 2,3-dihydro-1-oxo-2-(3-chlorophenyl)-1H-pyrrolo[3,4-b]quinoline (4c), 2,3-dihydro-1-oxo-2-(2-methylpheny)-1H-pyrrolo[3,4-b]quinoline (4d) and 2,3-dihydro-1-oxo-2-( 3-methylphenyl)-1H-pyrrolo[3,4-b]quinoline (4e), have been synthesized. In the synthetic processes, the key intermediate, ethyl 2-bromomethyl-3-quniolinecarboxylate generated from 2-nitrobenzaldehyde, reacts with various anilines to give ethyl 2-(phenylamino) methyl-3-quinolinecarboxylate (3a), ethyl 2-(2-chlorophenylamino)methyl-3-quinolinecarboxylate (3b), ethyl 2-(3-chlorophenylamino) methyl-3-quinolinecarboxylate (3c), ethyl 2-(2-methylphenylamino)methyl-3-quinolinecarboxylate (3d) and ethyl 2-(3-methylphenylamino)methyl-3-quinolinecarboxylate (3e). Compounds 3a, 3c and 3e were treated in potassium hydroxide solution to afford 4a, 4c and 4e, respectively. However, treatment of 3b and 3d under the same conditions afforded 2-(2-chlorophenylamino)methyl-3-quinolinecarboxylic acid (5b) and 2-(2-methylphenylamino) methyl-3-quinolinecarboxylic acid (5d), respectively. The ring closure products 4b and 4d could be obtained by the treatment of acids 5b and 5d with polyphosphoric acid, respectively.

关 键 词：Indoprofen类似物 合成 表征 闭环反应 Williamson反应 1-氧代-2-取代异二氢吲哚类化合物 消炎药 

分 类 号：TQ463[化学工程—制药化工]