A DFT study on the mechanism of the annulation reaction of trichloronitroethylene with aniline in the synthesis of quinoxalinone-N-oxides.
The new annulation reaction of trichloronitroethylene with aniline results in the formation of a quinoxalinone-N-oxide derivative. The mechanism of this one-pot annulation reaction between trichloronitroethylene (TCNiE) and anilines has been extensively investigated with B3LYP/6-31+G** methodology. Five different paths (1-5) were proposed and modeled by using this method. These paths were compared in terms of the activation energies of their rate-determining steps and in regard to the experimental findings. Paths 3 and 5, proceeding via four-membered heterocyclic rings, were found to be the most plausible paths with activation energies of 32 and 29 kcal/mol for the rate-determining steps, respectively. The effects of substituent, solvent, temperature, and computational method on these steps were also investigated. The results showed that path 5 is the most plausible mechanism for the annulation reaction of trichloronitroethylene with aniline.
Ozpinar
Gül A
GA
Department of Chemistry, Faculty of Science & Letters, Marmara University, Goztepe Campus, 34722 Istanbul, Turkey.
Erdem
Safiye S
SS
Meyer
Christian
C
Kaufmann
Dieter E
DE