关键词: 苯甲醛 P;喹啉 P;乙酯;苯胺 P;吡咯 P;元素分析, 红外分光光度法;质子磁共振谱法;质谱法

The Indoprofen analogues, including 2,3-dihydro-l-oxo-2-phenyl-l#- pyrcolo[3,4-6]qumoline (4a) and its congeners 2, 3-dihydro-l-oxo-2-(2- chloropheny)-l/f-pyrrolo[3, 4-6 ] quinoline (4b), 2, 3-dihydro-l-oxo-2- (3-chlorophenyl)-l#r-pyrrolo [3, 4-6 ] quinoline (4c), 2, 3-dihydro-l- oxo-2-(2-methylpheny)-ll/-pyrrolo [3, 4-6 ] quinoline (4d) and 2,3- dihydro-l-oxo-2-( 3-methylphenyl )-l//-pyrrolo [ 3, 4-6] 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 (Sd) , respectively. The ring closure products 4b and 4d could be obtained by the treatment of acids 5b and 5d with polyphosphoric acid, respectively.

Key words: BENZALDEHYDE P;QUINOLINE P;ETHYL ESTER;ANILINE P;PYRROLE P, ELEMENTAL ANALYSIS;IR;1HNMR;MS