Ultrasonic Aptitude of Regioselective Reaction of 6-bromo-spiro-3,1-benzoxazinone2,1′-isobenzofuran-3′,4-dione Towards Some Electrophilic and Nucleophilic Reagents

Abstract

In the present work, the 2-benzoxazinonyl benzoic acid (BBA) could be isomerized to the stereogenic spiro products (SBI) via ultrasonic and basic reaction conditions. The spiro compounds (SBI) have both electrophilic and nucleophilic centers. A series of nitrogen nucleophiles such as hydrazine hydrate, glycine, 2-aminopyridine, 2-picolinylamine, 4-anisidine, 4-aminoacetophenone and carbon electrophiles such as oxiranylmethylchloride, ethylchloroacetate, chloroacetylchloride, Mannich reagents, for example, formaldehyde with piperidine or morpholine can be treated with 2-benzoxazine-2-yl benzoic acid (BBA) via multicomponent reaction. The basicity of previous nucleophiles can be controlled on the course of reaction of 2-benzoxazinonyl benzoic acid. The chemical structure of the synthesized compounds can be confirmed by microanalytical, spectral data and optimized by quantum chemical parameters.