Three-component reaction involving isoquinoline and dimethyl acethylenedicarboxylate in the presence of indole: Theoretical and experimental investigations of the reaction mechanism

The reaction kinetics among isoquinoline, dimethyl acetylenedicarboxylate, and indole (as NH-acid) were investigated using ultraviolet (UV) spectrophotometry. The reaction rate equation was obtained, the dependence of the reaction rate on different reactants was determined, and the overall rate constant (kov) was calculated. By studying the effects of solvent, temperature, and concentration on the reaction rate, some useful information was obtained. A logical mechanism consistent with the experimental observations was proposed. Also, comprehensive theoretical studies were performed to evaluate the potential energy surfaces of all structures that participated in the reaction mechanism. Finally, the proposed mechanism was confirmed by the obtained results and the probable and logical reaction paths and also a correct product configuration were suggested based on the theoretical results.