Regioselective synthesis of spirooxindole-pyrolidine via (GAP) chemistry process: Experimental and DFT study

A series of the some spirooxindole-pyrrolidine derivatives were synthesized via 1,3-dipolar cycloadditions of isatin, (E)-2-oxoindolino-3-ylidene acetophenones and, primary/secondly amines with excellent yields, up to 97%, and high regioselectivity. To elucidate the disclosed regioselectivity, DFT computations using the B3LYP/6-31G (d,p) method were applied. It was discovered that this reaction superiorly prefers the kinetic product. Furthermore, the structural and vibrational characters of 4c, 4d, 4e, 4h and 4i were investigated incorporating the experimental FT-IR, 1H & 13C NMR spectra with DFT computations and sensible connections were acquired. Natural Bond Orbital (NBO) and HOMO-LUMO computation were done to calculate and anticipate their reactivities. The comparisons of the properties related to the chlorinated (4d) and methoxylated (4e) derivatives at the same levels of theory can be distinctly confirmed by the deactivating (Cl) and activating (OCH3) characteristics of the different groups linked to phenyl rings. The synthesized substances have been evaluated for their in vitro antioxidant, anticancer, and antibacterial activities, which some of them showed good activities compared to previously reported standard drugs