The syntheses and NMR spectra of the twelve isomeric thieno[b]fused naphthyridines

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Abstract
Through the use of Pd(0)‐catalyzed couplings between 2‐(2‐trimethylstannyl‐3‐pyridyl)‐1,3‐dioxolane, 3‐trimethylstannyl‐2‐pyridine carboxaldehyde, 3‐trimethylstannyl‐4‐pyridine carboxaldehyde and 4‐trimethyl‐stannyl‐3‐pyridine carboxaldehyde with t‐butyl‐N‐(3‐bromo‐2‐thienyl)carbamate, t‐butyl‐N‐(2‐bromo‐3‐thienyl)carbamate and t‐butyl‐N‐(4‐bromo‐3‐thienyl)carbamate in N,N‐dimethylformamide at 100°, using cupric oxide as a coreagent, all twelve isomeric thieno[b]naphthyridines have been synthesized in an one‐pot procedure. A detailed study of the 1H and 13C nmr spectra of these isomers has been undertaken.