Structural studies by 1H and 13C DNMR—II°: Alternative protonation sites in carbonyl conjugated chain enamines of the type R1-C1O-C2HC3H-NR2R3. A method of synthesis of disubstituted pyridinium salts

O-Protonation of secondary enamino ketones in TFA or concentrated mineral acids in various solvents is the kinetically favoured course of reaction leading ultimately to stable 2,5- or 3,4-disubstituted pyridinium salts. The mechanism of formation of the salts involves electrophilic attack by the C-3 carbon atom on C-2 or N-nucleophilic centres of the O-protonated molecule.