Vinamidinium salts as nucleophiles

2,3-Dihydro-1,4-diazepinium salts could not be aminomethylated with conventional methods, but the hydrochlorides produced with methyleniminium salts the C-Mannich-compounds. The reactivity of the substrate was mainly controlled by electronic effects of the substituents. Aminomethylation of 1,5-diazapentadienium salts occurred only if the conformations caused no steric hindrance of the beta-C-atom. Methyl substituted 2,3-dihydro-1,4-diazepinium salts reacted with 1,3,5 triazine to pyrimidine anellated derivatives.