Chemical and Pharmaceutical Bulletin · 1965 · 10 citations · 0 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryAnalgesic PharmacologyHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMacrocycle SynthesisHeterocyclic Medicinal ChemistryHydrogenationHydrogenation CatalysisIsoquinoline ChemistryIsoquinoline SynthesisLactam SynthesisMedicinal Chemistry ApplicationsMedicinal Heterocycles
In order to test the analgesic action of 2, 3, 4, 5-tetrahydro-6H-1, 5-methanobenzo-[f][1, 4]diazocine (III), methods for its synthesis were examined using various starting materials. Compounds (XIII, XVI, and XVII) were synthesized from isoquinoline (IV) via 4-aminoisoquinoline (VI). Cyclization of compounds (XIII, XVI, and XVII) gave the objective azabenzomorphane derivatives (XIV, III, and XVIII), respectively. Reduction of lactam (XVIII) with lithium aluminum hydride and debenzylation of XIV by catalytic hydrogenation in the presence of Adam's platinum afforded the same objective compound (III), which was also recognized as benzoyl and acetyl derivatives (XIV and XX).