Synthesis and spectral properties of 7-(p-bromophenyl)-10,10-dimethyl-8-alkylthio-7,9,10,11-tetrahydro-benz[c]acridines and deprotection-aromatization of 7-[(o-; and p-substituted)phenyl]-10,10-dimethyl-7,8,9,10,11,12-hexahydrobenz[c]acridin-8-thione

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-hexahydrobenz[c]acridin-8-one and Lawesson's reagent obtains the corresponding 7-[(o- and p-substituted)phenyl]-10,10-dimethyl-7,8,9,10,11,12-hexahydrobenz[c]acridin-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-benz[c]acridines 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-tetrahydrobenz[c]acridin-8-one IV, 1-6 and 7-[(o- and p-substituted)phenyl]-10,10-dimethyl-8-hydroxi-8,9,10,11tetrahydrobenz[c]acridine 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.