Heterocyclic analogs of pleiadiene. 54. Synthesis, basicities, and behavior with respect to electrophilic agents of 2-fluoromethyl- and 2-difluoromethyl-perimidines. Synthesis of perimidine-6(7)-carboxylic acids
Abstract2-Fluoromethyl derivatives of perimidine and 1-methylperimidine were obtained by the reaction of naphthalene-1,8-diamines with bromides of fluoroacetic acids. It is demonstrated in the case of acidic deuterium exchange and trifluoro-acetylation that the decrease in the basicity in the 2-methyl-, 2-fluoromethyl-,2-difluoromethyl-, and 2-trifluoromethylperimidine series promotes electrophilic substitution in the naphthalene ring. The previously unknown 6(7)-carboxylic acids of the perimidine series were obtained by alkaline hydrolysis of the trifluoroacetyl group.