Mechanistic Investigations for the Formation of Active Hexafluoroisopropyl Benzoates Involving Aza-Oxyallyl Cation and Anthranils

Herein, we report a multicomponent approach to access hexafluoroisopropyl activated esters using anthranil and aza-oxyallyl cation with hexafluoroisopropyl alcohol (HFIP) under mild reaction conditions. Activated (HFIP) esters synthesized via this approach serve as an important intermediate to obtain coveted 1,4-benzodiazepine-3,5-dione derivatives. The mechanism of the reaction was studied quantum mechanically using density functional theory (DFT) with functional M06-2X and 6-31G (d, p) basis set. Different pathways were investigated. Calculated results reveal probable involvement of two mechanisms in current transformation.