Azabenzomorphane and Related Compounds. VII. Synthesis of 1, 2, 3, 4, 5, 6-Hexahydro-2, 6-methanobenzo [d][1, 3] diazocine Derivatives

Abstract

In order to test the analgesic action of 1-methl-(XIa) and 1, 3-dimethyl-1, 2, 3, 4, 5, 6-hexahydro-2, 6-methanobenzo [d][1, 3] diazocine (XIb) were synthesized from 1-methyl-4-carboxymethylcarbostyril (III) as a starting material. Reductive cyclization of Xa and Xb with metallic sodium in ethanol gave, respectively, the expected azabenzomorphane derivatives, XIa and XIb. Furthermore, Ladenburg reduction of 1-methyl-4-carba-moylmethylcarbostyri (XII) also gave the above compound (XIa).