Nucleophilic-Substitution Reactions in Benzo[C][1,8]Naphthyridines

Abstract

The reactions of 1-chloro-3-methyl-6-(p- methylphenoxy ) benzo [c][1,8] naphthyridine with a variety of nucleophiles are reported. The relative reactivity of the 1- and 6-positions depends on the nucleophile and reaction conditions. Anilines, and alkyl and aryl thioxides react at position 1, alkylamines and alkoxide at position 6, and acidified alcohol at both 1 and 6. Some possible reasons for these positional reactivities are discussed.