A GENERAL-METHOD OF SYNTHESIS OF REGIOSPECIFICALLY N-OXIDIZED OR N-QUATERNIZED POLYAZINES BY PALLADIUM-CATALYZED CROSS-COUPLING OF N-OXIDIZED OR N-QUATERNIZED HETARYL STANNANES

N-Oxides of tributylstannylated pyridine, quinoline, and isoquinoline and tributylstannylated N-methiodides of pyridine and quinoline were r eadily prepared, many for the first time. In the presence of a palladi um catalyst these materials were cross-coupled to various chloro, brom o, and iodo hetaryl halides to give polyazines having the N-functional group placed unequivocally in eleven different polycyclic ring system s. The use of tosylate as a counterion with quaternized salts minimize d decomposition of the stannane.