Synthesis and spectral properties of 7-(p-bromophenyl)-10,10-dimethyl-8-alkylthio-7,9,10,11-tetrahydro-benzcacridines and deprotection-aromatization of 7-(o-; and p-substituted)phenyl-10,10-dimethyl-7,8,9,10,11,12-hexahydrobenzcacridin-8-thione

摘要

A series of sixteen new derivatives have been obtained and all have potentially useful pharmacological activity. The treatment of 7-(o-chloro and p-bromo)phenyl-7,8,9,10,11,12-hexahydrobenzcacridin-8-one and Lawesson's reagent obtains the corresponding 7-(o- and p-substituted)phenyl-10,10-dimethyl-7,8,9,10,11,12-hexahydrobenzcacridin-8-thione II which was alkylated in presence of sodium hydride and the corresponding alkyl iodide under nitrogen atmosphere to obtain 8-alkylthio-7,9,10,11-tetrahydro-benzcacridines III, 1-4. The thione 11 was desprotected and aromatized in presence of sodium hydride in absence of nitrogen atmosphere to produce a mixture of 7-(o- and p-substituted)phenyl-10,10-dimethyl-8,9,10,11-tetrahydrobenzcacridin-8-one IV, 1-6 and 7-(o- and p-substituted)phenyl-10,10-dimethyl-8-hydroxi-8,9,10,11tetrahydrobenzcacridine V, 1-6. The structure of all products was corroborated by ir, H-1 NMR, C-13 NMR with bidimensional experiments and ms with CID experiments.