Mechanistic Investigations for the Formation of Active Hexafluoroisopropyl Benzoates Involving Aza‐Oxyallyl Cation and Anthranils
Anirban Mukherjee, Arshad J. Ansari, S. Rajagopala Reddy, Gourab Kanti Das, Ritesh Singh
Abstract
Abstract 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.
Topics & Concepts
ChemistryBenzoatesDensity functional theoryAlcoholComputational chemistryReaction mechanismMechanism (biology)Basis setCombinatorial chemistryOrganic chemistryCatalysisPhilosophyEpistemologySynthesis and Biological EvaluationMulticomponent Synthesis of HeterocyclesSynthesis and Reactions of Organic Compounds