Isoindoline Derivatives of Opianic Acid

Abstract

AbstractThe participation of a neighbouring carboxylic group in acetylation reactions of aldehyde acylhydrazones and imines was investigated. Acetylation reactions of the 6‐formyl‐2,3‐dimethoxybenzoic acid hydrazones 6b, f– h, j and imine 6a yielded 2‐substituted 3‐acetoxyisoindolinones (9i– n and 10e, respectively). Under similar conditions, the thiosemicarbazone 6i afforded the thiadiazoloisoindole derivative 11. The structures of the products were proved by spectroscopic evidence and through unambiguous syntheses via the corresponding 3‐chloro‐ and 3‐hydroxyisoindolinone derivatives (9a– e and 10a– d, respectively). The syntheses of some symmetrical products (12 and 14– 17) are also described. The racemates 9– 12 and 15– 17 were not separated into the enantiomers.