Synthesis of N-(p-aminobenzoyl)-1,2,3,4-tetrahydroquinoline and derivatives

Abstract

The present investigation was to study and develop the synthetic routes of N-(p-aminobenzoyl)-1,2,3,4-tetrahydroquinolines, the new series of organic compounds, designed by using ameltolide as the lead agent. These rigid analogues of ameltolide were expected to possess anticonvulsant activity. Eight compounds in this new series (CU-17-02, Cu-17-04, CU-17-06, CU-17-08, CU-17-10, CU-17-12, CU-17-14 and CU-17-16) were successfully prepared as followed: First, a number of substituted quinolines, synthesized by modified Skraup reaction, were reduced to their corresponding 1,2,3,4-tetrahydroquinolines by using sodium-borohydride nickelous chloride system. Then, N-acylation of the resulting 1,2,3,4-tetrahydroquinolines with p-nitrobenzoyl chloride followed by catalytic hydrogenation yield the target compounds, N-(p-aminobenzoyl)-1,2,3,4-tetrahydroquinolines. The structures of the synthesized compounds were confirmed by infrared spectrometry, mass spectrometry, nuclear magnetic resonance spectrometry and elemental analysis techni techniques.