Synthesis of certain 4-oxo-1.2.3.4-tetrahydroquinoline and benzazocine derivatives likely to possess analgesic activity.
Cyanoethylation of anthranilic acid afforded the N-cyanoethyl derivative which on treatment with ethanolic and methanolic hydrogen chloride yielded the corresponding diethyl and dimethyl esters respectively. Application of the Dieckmann's conditions to the N-acetyl derivatives of the two esters using sodium hydride and sodium ethoxide afforded different products. With the former, the expected products were obtained, while with the latter catalyst both esters furnished one and the same compound which was shown to be a benzazocine trione. The structure of the azocine was inferred from elemental analysis, spectroscopic data and formation of derivatives.
D000700:Analgesics / Q000138:chemical synthesis*; D001392:Azocines / Q000138:chemical synthesis*; D002384:Catalysis; D055598:Chemical Phenomena; D002621:Chemistry; D011804:Quinolines / Q000138:chemical synthesis*
D000700:Analgesics; D001392:Azocines; D011804:Quinolines