Synthesis of novel benzo[h][1,6]naphthyridine derivatives from 4-aminoquinoline and cyclic β-ketoester

This paper describes the synthesis of 2,8-dichloroquinolin-4-amine 4 and 4,5,7-trichloro-3-(2-chloroethyl)-2-methylbenzo[h][1,6]naphthyridine 8 as novel class of building blocks. Also describes the regioselective S_NAr reactions of 2,4,8-trichloroquinoline 2 on C₂ and C₄ positions with azide, similarly S_NAr reactions of benzo[h][1,6]naphthyridine 8 at C₄, C₅ positions, and S_N2 reactions on C₃-(2-chloroethyl) side chain with nucleophiles such as primary aromatic amines, methoxide/ethoxide, and azide at different temperatures.