On the behavior of α‐brominated dimethyl o‐benzenediacetate toward nitrogen nucleophiles . Part I. Reaction of dimethyl α,α'‐dibromo o‐benzenediacetate with hydrazines

Abstract

AbstractMeso‐ (1a) and racemic dimethyl α,α'‐dibromo o‐benzenediacetate (1b) when condensed with hydrazine and methylhydrazine furnished respectively 1,3‐dicarbomethoxyisoindole (5a) and its N‐methyl derivative (5b). Reaction of phenylhydrazine with 1a led to the N‐phenylisoindole (5c) and to the N‐anilino isoindoline (6) as the cis isomer; conversely, 1b was transformed into a mixture of the 2‐phenyl‐1,2,3,4‐tetrahydrophthalazine (7), the trans isomer of (6), the N‐anilinoisoindole (5d) and dimethyl α‐(N'‐phenylhydrazino)‐o‐benzenediacetate (8). Compounds 1a and 1b were also condensed with acetylhydrazine to give a mixture of the N‐acetylaminoisoindoline (12) and of the 2‐acetyl‐1,2,3,4‐tetrahydrophthalazine (13).