The Role of the Catalyst on the Reactivity and Mechanism in the Diels–Alder Cycloaddition Step of the Povarov Reaction for the Synthesis of a Biological Active Quinoline Derivative: Experimental and Theoretical Investigations

An experimental and theoretical study of the reactivity mechanism non-catalyzed catalyzed Povarov reaction for preparation a 4-ethoxy-2,3,4,4a-tetrahydro-2-phenylquinoline as biological active quinoline derivative has been performed. The optimization conditions indicate that use catalyst, namely Lewis acid with an electron-releasing group, creates best this kind reaction. chemical structure was characterized by usual spectroscopic methods. prepared also tested in vitro antibacterial activity, which displays moderate inhibitory activity against both Escherichia coli Staphylococcus aureus. antioxidant investigated evaluating their 1,1-diphenyl-2-picrylhydrazyl DPPH radical, reveals high reactivity. computational performed on Diels–Alder step using B3LYP/6-31G(d,p) level theory. conceptual DFT indices explain well meta regioselectivity experimentally observed. Both catalysts enhance imine, favoring formation regioisomers low activation energy, they change to highly synchronous stepwise Brønsted acid. imine allyl alcohol does not give any product, requires energy.