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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.

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The reaction of methylbenzo[h] [1,6]naphthyridine (1) with thiourea yield 4-chloro-12-methyl-16,17-dihydro-15-thia-6,11-diazacyclopenta[a]phenanthrene-7-thiol (2). The chemistry of compound 2 is explored to obtained iminothioether derivatives (3a-h) in good yields. The structures of newly synthesized compounds were confirmed by spectral data and elemental analysis. The antimicrobial activity of newly synthesized compounds were studied against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Pseudomonas aeroginosa, Proteus valgaris, Bacillus cereus, Streptococcus sp. and Bacillus megaterium by the agar well diffusion method. Compounds 3d, 3f and 3h showed moderate antimicrobial activity.