Benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines: synthesis, mechanistic studies, and crystal structure determination

摘要

New benzothiazolyl- and benzimidazolyl-substituted 1-iminoisoindolines are prepared in the reaction of o-phthalaldehyde and substituted 2-aminobenzothiazoles and 2-aminobenzimidazoles. The optimization of these reactions is discussed, and the reaction mechanisms are proposed based on the experimental findings. Isoindolines with other heterocyclic substituents are prepared as a confirmation of the proposed mechanisms. Molecular and crystal structures of several prepared compounds are determined by a single crystal X-ray diffraction. These structures are found to be in line with projections based on the chemical and spectroscopic properties, and thus offer an additional confirmation of the proposed reaction mechanisms.