Phthalimides. III. Ammonolysis, Aminolysis, Hydrazinolysis, Pyrolysis, and Action of Grignard Reagents on Phthalimide Derivatives

Abstract N-Hydroxyphthalimide undergoes ammonolysis to give phthalimide. N-(Aroyloxy)phthalimides undergo alcoholysis followed by ammonolysis to give mixtures of phthalimide and ester. N-(Arylsulfonyloxy)phthalimides undergo ammonolysis, followed by Lossen rearrangement to give mixtures of 2,4-quinazolinedione and ammonium salts of arenesulfonic acids. N-Hydroxyphthalimide undergoes aminolysis to give the corresponding N-arylphthalimides. N-Hydroxyphthalimide reacts with hydrazine hydrate and/or phenylhydrazine in acetic acid or ethanol to give the corresponding 1,4-phthalazinedione, or by fusion to give phthalimide and N-phenylphthalimide, respectively. Pyrolysis of N-hydroxyphthalimide gives phthalimide, and N-(aroyloxy)phthalimides give mixtures of phthalimide and carboxylic acids. N-(Arylsulfonyloxy)phthalimides give mixture of phthalimide and arenesulfonic acids. However, pyrolysis of N-(arylcarbamoyloxy)phthalimides gave N-arylphthalimides. N-Hydroxyphthalimide reacts with phenylmagnesium bromide to give 1,1-diphenyl-3-(phenylimino)-1,3-dihydroisobenzofuran via ring opening followed Beckmann rearrangement, while N-(arylsulfonyloxy)phthalimides react with arylmagnesium bromide to give mixtures of [O-(arylamino)phenyl]diarylmethanols, and arenesulfonic acids via ring opening followed by Lossen rearrangement.