Theoretical study on l-proline-catalyzed intramolecular cyclization of aminoketone and aldehyde to quinolinone derivatives

Abstract

Mechanisms of synthetic reaction of 2-aryl-2,3-dihydroquinolin-4(1H)-ones (P1) and its derivatives, 2-(4-chloro-phenyl)-2,3-dihydroquinolin-4(1H)-one (P2), 2-(4-fluoro-phenyl)-2,3-dihydroquinolin-4(1H)-one (P3) and 2-(4-methyl-phenyl)-2,3-dihydroquinolin-4(1H)-one (P4) catalyzed by L-proline have been investigated using density functional theory method. Energy, rate constants, equilibrium constants and thermodynamic properties for all reaction steps were obtained at the B3LYP/ 6-31+G(d,p) and B3LYP/6-31G(d) levels of theory. Synthetic reactions for all quinolinone derivatives are an exothermic process and composed of seven reaction steps. Rate determining step of synthetic reactions for products P1, P2, P3 and P4 are their third step and rate constants are 8.37x10[superscript -25],1.22x10 [superscript -24], 6.60x10 [superscript -25] and 9.64 x 10 [superscript -1], respectively.