N-Aminopyridinium salts bearing ester, aroyl, and cyano functions in position 2 as well as their differently annelated benzologues were reacted with hydroxide ion and alkoxides. In the case of ester compounds 1, 3, and 5, transesterification and dimerization reactions were found. Keto salts 7, 13, and 15 showed dimerization reactions coupled with methanolysis. Monocyclic cyano salt 17 gave amino-as-triazinium double salt 20 while the benzologues ...