Chemistry of the phenoxathiins and isosterically related heterocycles. XII. Synthesis of diazaphenoxathiin analogs: 1,9‐Diazaphenoxathiin and 1,7‐diazaphenoxathiin

Abstract

Abstract The synthesis of the first diazaphenoxathiins, 1,9‐diazaphenoxathiin and 1,7‐diazaphenoxathiin, are described. Complete assignments are made for the 13 C‐nmr spectra of these compounds based on additivity correlation and 1 H‐ 13 C spin‐coupling constants. The isolation and confirmation of the structure of 2‐[2′(‐3′‐nitropyridylthio)]‐3‐[2″‐(3″‐nitropyridyloxy)] pyridine using 13 C‐nmr and appropriate model compounds is also discussed. A preliminary evaluation of spontaneous motor depression in mice showed a substantial difference between the observed activities of the two diazaphenoxathiins reported. The possibility of the observed difference being associated with the relative positions of the annular aza‐substitutions is discussed.