Semistabilized diazatrienyl anions are generated by the
reaction
of 2-pyridylarylimines with arylacetylenes in superbase systems MO
t
Bu (M = Li, Na, K)/DMSO at ambient temperature
for 15 min. The initial intermediate N-centered propargyl-1,3-diaza-1,3,5-trienyl
anions undergo intermolecular cyclization to benzyl imidazopyridine
anions (formally [3 + 2] cycloaddition), further intercepting a second
molecule of the starting pyridylimines or a proton of medium to afford
(Z)-stilbene/imidazopyridine ensembles and benzyl
imidazopyridines. The charge distribution in all intermediate anions
and their synthetic evolution are consistent with quantum-chemical
analysis (B2PLYPD/6-311+G**//B3LYP/6-31+G*).