Synthesis of thienothiazocinoisoindolediones and thienothiazinoisoindolones from mercaptothiophenes and chloromethylphthalimide

Abstract

Abstract 2‐Thienylthiomethylphthalimides 3a,b were synthesized by action of Chloromethylphthalimide on 2‐or 3‐mercaptothiophene. Reduction of 3a,b and Wittig reaction using carbethoxycarbonyltriphenyl‐phosphorane gave the corresponding acetic acids 5a,b which cyclized under Friedel and Crafts conditions to lead the thienothiazocinoisoindolediones 6a,b. Thienothiazinoisoindolones 7a,b were obtained from hydroxyisoindolones derivatives 4a,b in acid conditions via an acyliminium ion.