Site-selective formation of N-arylmethylimidazoles and C-arylimines in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with aromatic aldehydes

Regioselective formation of N-arylmethylimidazoles and C-arylimines was found in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with selected aromatic aldehydes. The regiochemistry of the reaction products was confirmed by single crystal X-ray analysis. Gibbs free energy calculation using DFT method at the B3LYP/6-31G(d) level supports the regio-selectivity observed. The 4-imine obtained in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with pyrene-1-carboxaldehyde showed an unusually low magnetic field shift of the imine proton that was reproduced by molecular calculations.