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Suzuki-Miyaura cross coupling was successfully used for C5-arylation in 4-amino-2-chloroquinoline-3-carbaldehyde using arylbornic acid and tetrakistriphenylphosphine palladium catalyst in water. Friedländer condensation reaction on 4-amino-2-chloro/2-arylquinoline-3-carbaldehyde and aromatic ketones gave novel aryl and diarylbenzo[h] [1, 6]naphthyridines in good yields. Fluorescence quantum yields were increased by introducing C2 and C5 π donor aryl benzo[h][1, 6]naphthyridines derivatives., (© Springer Science+Business Media, LLC 2011)

Abstract: 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 SNAr reactions of 2,4,8-trichloroquinoline 2 on C2 and C4 positions with azide, similarly SNAr reactions of benzo[h][1,6]naphthyridine 8 at C4, C5 positions, and SN2 reactions on C3-(2-chloroethyl) side chain with nucleophiles such as primary aromatic amines, methoxide/ethoxide, and azide at different temperatures. [Copyright &y& Elsevier]