Synthesis of 2,2-dimethyl-1,2-dihydrobenzo[f]-isoquinolines displaying antifungal activity

Article abstract of DOI:10.1007/s10593-011-0694-3

The reaction of 2,2-dimethyl-1,2-dihydrobenzo[f]isoquinoline with malonic acid gave (2,2-dimethyl-1,2,3,4-tetrahydrobenzo[f]isoquinolin-4-yl)acetic acid, the acid chloride of which readily forms esters with alcohols and phenols. Reaction of the same azomethine with thioglycolic acid leads to (2,2-di-methyl-1,2,3,4-tetrahydro-benzo[f]isoquinolin-4-yl)thioacetic acid. Activation of the initial azomethine by iodomethylation enables reaction with 1,3-indanedione to be carried out. The obtained substances display antifungal action.